Phenyl-substituted bicyclooctane-1,3-dione-derivatives

ABSTRACT

The invention relates to novel compounds of the formula (I) 
                         
in which R 1 , R 2 , R 3 , R 4 , R 5 , Y, Q and G have the meanings given above,
 
to a plurality of processes and intermediates for their preparation and to their use as herbicides and/or pesticides.
 
     Moreover, the invention relates to selective herbicidal compositions comprising, firstly, the phenyl-substituted bicyclooctane-1,3-dione derivates and, secondly, a crop plant compatibility-improving compound. 
     The present invention furthermore relates to increasing the activity of crop protection compositions comprising in particular phenyl-substituted bicyclooctane-1,3-dione derivates by adding ammonium salts or phosphonium salts and, if appropriate, penetrants, to the corresponding compositions, to processes for their preparation and to their use in crop protection as pesticides and/or for preventing unwanted plant growth.

CROSS REFERENCE TO RELATED APPLICATIONS

This application is a §371 National Stage Application ofPCT/EP2011/069040, filed Oct. 28, 2011, which claims priority toEuropean Application No. 10189670.2, filed Nov. 2, 2010, and U.S.Provisional Application filed Nov. 2, 2010.

BACKGROUND OF THE INVENTION

1. Field of the Invention

The present invention relates to novel phenyl-substitutedbicyclooctane-1,3-dione derivatives, to a plurality of processes fortheir preparation and to their use as herbicides and/or pesticides.

2. Description of Related Art

Moreover, the invention relates to novel selective herbicidal activecompound combinations comprising, firstly, phenyl-substitutedbicyclooctane-1,3-dione derivates and, secondly, at least one crop plantcompatibility-improving compound, which combinations can be used withparticularly good results for the selective control of weeds and variouscrops of useful plants.

The present invention furthermore relates to increasing the activity ofcrop protection compositions comprising in particular phenyl-substitutedbicyclooctane-1,3-dione derivates by adding ammonium salts orphosphonium salts and, if appropriate, penetrants, to the correspondingcompositions, to processes for their preparation and to their use incrop protection as insecticides and/or for preventing unwanted plantgrowth.

It is known that certain substituted 2-arylcyclopentanediones haveherbicidal, insecticidal and acaricidal properties (cf., for example,U.S. Pat. Nos. 4,283,348; 4,338,122; 4,436,666; 4,526,723; 4,551,547;4,632,698; WO 96/01 798; WO 96/03 366, WO 97/14 667 and also WO98/39281, WO 99/43649, WO99/48869, WO 99/55673, WO 01/17972, WO01/74770, WO 03/062244, WO 04/080962, WO04/111042, WO05/092897,WO06/029799, WO07/080,066, WO07/096,058, WO 09/019,005, WO 09/019,015,WO 10/000,773, WO 10/081,894, WO 10/089,210 and WO 10/040,460). Alsoknown are compounds which are substituted in a similar way:3-hydroxy-5,5-dimethyl-2-phenylcyclopent-2-en-1-one from the publicationMicklefield et. al., Tetrahedron, (1992), 7519-26 and the naturalproduct Involution(−)-cis-5-(3,4-dihydroxyphenyl)-3,4-dihydroxy-2-(4-hydroxyphenyl)-cyclopent-2-enonefrom the publication Edwards et al., J. Chem. Soc. S, (1967), 405-9. Aninsecticidal or acaricidal action is not described. Moreover,2-(2,4,6-trimethylphenyl)-1,3-indanedione is known from the publicationJ. Economic Entomology, 66 (1973), 584 and the laid-open publicationDE-A 2 361 084 (U.S. Pat. No. 4,091,006), with herbicidal and acaricidalactions being stated.

However, in particular at low application rates and concentrations, theactivity and activity spectrum of these compounds is not always fullysatisfactory. Furthermore, the compatibility of these compounds withplants is not always sufficient.

SUMMARY

This invention now provides novel compounds of the formula (I)

in whichif

-   Q represents a bond, a C₁-C₃-alkylene, a C₂-C₃-alkenylene or a    C₂-C₃-alkynylene chain,    then-   Y represents the groups —OR⁶, —S(O)_(p)R⁶, —CO₂R⁷, —CH═CH₂, cyano,    —SCN, —CONR⁸R⁹, —SO₂NR⁸R⁹, CR¹⁰═O, —NR¹¹R¹², —CR¹⁰═N—OR¹³,    —CR¹⁰═N—R¹⁴, CR¹⁰═N—NR¹⁵R¹⁶, —CR¹⁰(OR¹⁷OR¹⁸), —CR¹⁰(SR¹⁷OR¹⁸),    —CR¹⁰(SR¹⁷SR¹⁸), —CR¹⁰(NHR¹⁷NHR¹⁸), —CR¹⁰(NHR¹⁷OR¹⁸),    —CR¹⁰(NHR¹⁷SR¹⁸), —CH(CN)₂, —CH(OH)R⁶, halogen, —O(C=M)R¹⁰,    —S(C=M)R¹⁰, —O(C=M)NR¹¹R¹², —S(C=M)NR¹¹R¹², —NH(C=M)NR¹¹R¹²,    —O(C=M)OR⁷, —S(C=M)OR⁷, —NH(C=M)OR⁷ or represents the group W,-   or Q, Y and R⁵ together form one of the groups CHCN═,    CH(CO₂C₁-C₆-alkyl)═,

-   W represents a 3- to 7-membered saturated or partially saturated    heterocycle which contains at least one heteroatom such as oxygen,    sulphur or nitrogen and may additionally be mono- or polysubstituted    by identical or different substituents,-   G represents hydrogen, methyl, ethyl or benzyl (a) or represents one    of the groups

-   E represents a metal ion equivalent, a tertiary sulphonium ion or an    ammonium ion,-   L represents oxygen or sulphur,-   M represents oxygen or sulphur,-   R¹ represents hydrogen, halogen, cyano, nitro, C₁-C₆-alkyl,    halo-C₁-C₆-alkyl, C₃-C₆-cycloalkyl, halo-C₃-C₆-cycloalkyl,    C₂-C₆-alkenyl, halo-C₂-C₆-alkenyl, C₂-C₆-alkynyl,    halo-C₂-C₆-alkynyl, C₁-C₆-alkoxy, halo-C₁-C₆-alkoxy,    C₃-C₆-cycloalkoxy, halo-C₃-C₆-cycloalkoxy, C₂-C₆-alkynyloxy,    halo-C₂-C₆-alkynyloxy, C₂-C₆-alkenyloxy, halo-C₂-C₆-alkenyloxy,    C₁-C₃-alkylthio, C₁-C₃-alkylsulphinyl, C₁-C₃-alkylsulphonyl,    halo-C₁-C₃-alkylthio, halo-C₁-C₃-alkylsulphinyl or    halo-C₁-C₃-alkylsulphonyl,-   R² and R³ independently of one another are identical or different    and represent hydrogen, halogen, cyano, nitro, C₁-C₆-alkyl,    halo-C₁-C₆-alkyl, C₂-C₆-alkenyl, halo-C₂-C₆-alkenyl, C₂-C₆-alkynyl,    halo-C₂-C₆-alkynyl, C₁-C₆-alkoxy, halo-C₁-C₆-alkoxy,    C₃-C₆-cycloalkyl, C₃-C₆-cycloalkoxy, halo-C₃-C₆-cycloalkoxy,    C₂-C₆-alkynyloxy, halo-C₂-C₆-alkynyloxy, C₂-C₆-alkenyloxy,    halo-C₂-C₆-alkenyloxy, C₁-C₃-alkylthio, C₁-C₃-alkylsulphinyl,    C₁-C₃-alkylsulphonyl, halo-C₁-C₃-alkylthio,    halo-C₁-C₃-alkylsulphinyl, halo-C₁-C₃-alkylsulphonyl, phenyl or    phenyl which is optionally mono- or polysubstituted by identical or    different substituents from the group consisting of halogen,    C₁-C₄-alkyl, halo-C₁-C₄-alkyl, C₃-C₆-cycloalkyl,    halo-C₃-C₆-cycloalkyl, C₁-C₆-alkoxy, halo-C₁-C₆-alkoxy, nitro and    cyano,-   R⁴ represents hydrogen, halogen, cyano, nitro, C₁-C₆-alkyl,    halo-C₁-C₆-alkyl, C₃-C₆-cycloalkyl, halo-C₃-C₆-cycloalkyl,    C₁-C₆-alkoxy, halo-C₁-C₆-alkoxy, C₃-C₆-cycloalkoxy, or    halo-C₃-C₆-cycloalkoxy,-   R⁵ represents hydrogen or C₁-C₄-alkyl,-   R⁶ represents hydrogen, C₁-C₆-alkyl, halo-C₁-C₆-alkyl,    C₃-C₆-cycloalkyl, halo-C₃-C₆-cycloalkyl, C₂-C₆-alkenyl,    halo-C₂-C₆-alkenyl, C₂-C₆-alkynyl, halo-C₂-C₆-alkynyl,    C₁-C₄-alkoxy-C₁-C₄-alkyl, halo-C₁-C₄-alkoxy-C₁-C₄-alkyl,    C₃-C₆-cycloalkoxy-C₁-C₄-alkyl, halo-C₃-C₄-cycloalkoxy-C₁-C₄-alkyl,    represents benzyl, phenyl, heteroaryl, —CH₂-heteroaryl,    —CH₂CH₂-heteroaryl, pyranyl, tetrahydrofuranyl, C₁-C₄-alkanoyl,    halo-C₁-C₄-alkanoyl, benzoyl, each of which is optionally mono- or    polysubstituted by identical or different substituents from the    group consisting of halogen, cyano, nitro, C₁-C₆-alkyl,    halo-C₁-C₆-alkyl, C₃-C₆-cycloalkyl, halo-C₃-C₆-cycloalkyl,    halo-C₂-C₆-alkenyl, C₂-C₆-alkynyl, halo-C₂-C₆-alkynyl,    C₁-C₄-alkoxyalkyl, halo-C₁-C₄-alkoxy-C₁-C₆-alkyl,    C₃-C₆-cycloalkoxy-C₁-C₆-alkyl and    halo-C₃-C₆-cycloalkoxy-C₁-C₆-alkyl, or represents benzoyl, which is    optionally mono- or polysubstituted by identical or different    substituents from the group consisting of halogen, cyano, nitro,    C₁-C₆-alkyl, halo-C₁-C₆-alkyl, C₃-C₆-cycloalkyl and    halo-C₃-C₆-cycloalkyl,-   R⁷ represents hydrogen, represents in each case optionally    substituted C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₂-C₆-alkenyl or    represents a cation E,-   R⁸ and R⁹ independently of one another are identical or different    and represent hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,    C₃-C₆-cycloalkyl, phenyl, benzyl, represent phenyl or benzyl, each    of which is mono- or polysubstituted by identical or different    substituents from the group consisting of halogen, nitro, cyano and    C₁-C₃-alkyl or-   R⁸ and R⁹ together with the adjacent nitrogen atom form a    morpholino, piperidino or pyrrolidino group,-   R¹⁰ represents hydrogen, C₁-C₆-alkyl, halo-C₁-C₄ alkyl,    C₂-C₆-alkenyl, halo-C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl,    represents phenyl or benzyl, each of which is optionally mono- or    polysubstituted by identical or different substituents from the    group consisting of halogen, C₁-C₆-alkyl and halo-C₁-C₆-alkyl,-   R¹¹ and R¹² independently of one another are identical or different    and represent hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,    C₃-C₆-cycloalkyl, phenyl, benzyl, represent phenyl or benzyl, each    of which is mono- or polysubstituted by identical or different    substituents from the group consisting of halogen, nitro, cyano and    C₁-C₃-alkyl or-   R¹¹ and R¹² together with the adjacent nitrogen atom form a    morpholino, piperidino or pyrrolidino group,-   R¹³ represents hydrogen or represents C₁-C₆-alkyl, C₂-C₆-alkenyl,    C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyl-C₁-C₃-alkyl, each    of which is optionally interrupted once or more by oxygen or sulphur    and is optionally mono- or polysubstituted by halogen, represents    benzyl or —CH₂-heterocyclyl, each of which is optionally mono- or    polysubstituted by identical or different substituents from the    group consisting of halogen, nitro, cyano and C₁-C₃-alkyl,-   R¹⁴ represents hydrogen, C₁-C₆-alkyl, halo-C₁-C₆-alkyl,    C₂-C₆-alkenyl, halo-C₂-C₆-alkenyl, C₂-C₆-alkynyl,    halo-C₂-C₆-alkynyl, phenyl, benzyl or represents phenyl or benzyl,    each of which is mono- or polysubstituted by identical or different    substituents from the group consisting of halogen, C₁-C₃-alkyl,    halo-C₁-C₃-alkyl, C₃-C₆-cycloalkyl, halo-C₃-C₆-cycloalkyl, nitro and    cyano,-   R¹⁵ and R¹⁶ independently of one another are identical or different    and represent hydrogen, C₁-C₅-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,    C₃-C₆-cycloalkyl, phenyl, benzyl, represent phenyl or benzyl, each    of which is mono- or polysubstituted by identical or different    substituents from the group consisting of halogen, nitro, cyano and    C₁-C₃-alkyl or-   R¹⁵ and R¹⁶ together with the adjacent nitrogen atom form a    morpholino, piperidino or pyrrolidino group,-   R¹⁷ represents hydrogen, represents C₁-C₆-alkyl, benzyl or    halo-C₁-C₆-alkyl, each of which is optionally interrupted once or    more by identical or different radicals from the group consisting of    oxygen and sulphur,-   R¹⁸ represents hydrogen, represents C₁-C₆-alkyl, benzyl or    halo-C₁-C₆-alkyl, each of which is optionally interrupted once or    more by identical or different radicals from the group consisting of    oxygen and sulphur,-   R¹⁹ represents optionally halogen-substituted C₁-C₆-alkyl,    C₂-C₆-alkenyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,    C₁-C₃-alkylthio-C₁-C₄-alkyl, poly-C₁-C₄-alkoxy-C₁-C₄-alkyl or    represents C₃-C₆-cycloalkyl which is optionally mono- or    polysubstituted by identical or different substituents from the    group consisting of halogen, C₁-C₄-alkyl and C₁-C₄-alkoxy and may    optionally be interrupted in the ring by oxygen or sulphur,    represents phenyl, phenyl-C₁-C₄-alkyl, hetaryl, phenoxy-C₁-C₄-alkyl    or hetaryloxy-C₁-C₄-alkyl, each of which is optionally substituted    by halogen or C₁-C₄-alkyl,-   R²⁰ represents C₁-C₆-alkyl, C₂-C₆-alkenyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,    poly-C₁-C₄-alkoxy-C₁-C₄-alkyl, each of which is optionally mono- or    polysubstituted by identical or different halogen, or represents    C₃-C₆-cycloalkyl which may optionally be interrupted in the ring by    oxygen or sulphur, or represents benzyl,-   R²¹, R²² and R²³ independently of one another are identical or    different and represent C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-alkylamino,    C₁-C₆-dialkylamino, C₁-C₃-alkylthio, C₂-C₄-alkenylthio,    C₃-C₆-cycloalkylthio, each of which is optionally mono- or    polysubstituted by identical or different halogen, or represent    phenyl, benzyl, phenoxy or phenylthio,-   R²⁴ and R²⁵ independently of one another are identical or different    and represent hydrogen, represent C₁-C₆-alkyl, C₃-C₆-cycloalkyl,    C₂-C₆-alkenyl, C₁-C₆-alkoxy, C₁-C₆-alkoxy-C₁-C₄-alkyl, each of which    is optionally mono- or polysubstituted by identical or different    halogen, represent phenyl or benzyl, optionally mono- or    polysubstituted by identical or different substituents from the    group consisting of halogen and C₁-C₄-alkyl or-   R²⁴ and R²⁵ together with the adjacent nitrogen atom form a    morpholino, piperidino or pyrrolidino group,-   p represents the number 0, 1 or 2,    or if-   Q, Y and R⁵ together represent the group CH₂═, then-   G represents methyl, ethyl or benzyl (a).

Substituent G may be attached according to formula (I-A), (I-B) or(I-C).

DETAILED DESCRIPTION OF A PREFERRED EMBODIMENT

In this context, the term “halogen” comprises fluorine, chlorine,bromine and iodine.

The terms “alkyl”, “alkenyl” and “alkynyl” are to be understood asmeaning both straight-chain and branched hydrocarbon radicals.

Depending inter alia on the nature of the substituents, the compounds ofthe formula (I) may be present as geometric and/or optical isomers orisomer mixtures of varying composition which, if appropriate, may beseparated in a customary manner. The present invention provides both thepure isomers and the isomer mixtures, their preparation and use andcompositions comprising them. However, for the sake of simplicity,hereinbelow only compounds of the formula (I) are referred to, althoughwhat is meant is both the pure compounds and, if appropriate, mixtureshaving various proportions of isomeric compounds.

Depending on the position of the substituent G, the compounds of theformula (I) can be present in the two isomeric forms of the formulae(I-A) and (I-B)

which is meant to be indicated by the broken line in formula (I).

For the specific case in which the substituent G in the formula (I) ishydrogen, an additional isomeric form may also be present having theformula (I-C)

The compounds of the formulae (I-A), (I-B) and (I-C) can be present bothas mixtures and in the form of their pure isomers. If appropriate,mixtures of the compounds of the formulae (I-A), (I-B) and (I-C) can beseparated by physical methods, for example by way of chromatographicmethods.

For reasons of clarity, hereinbelow only one of the possible isomers isshown in each case. This does not exclude that, if appropriate, thecompounds may be present in the form of the isomer mixtures or in therespective other isomeric form.

For reasons of simplicity, in the case of the compounds of the formula(I-a), in most cases only the isomeric form (I-C), in which G representshydrogen, is shown. However, in the compounds of the formula (I-a), theG substituent may also represent methyl, ethyl or benzyl, in which casethe compounds are present in the isomeric forms (I-A) and (I-B).

Including the different meanings (a), (b), (c), (d), (e), (f) and (g) ofgroup G, the following principle structures (I-a) to (I-g) result:

in which

-   Q, Y, E, L, M, R¹, R², R³, R⁴, R⁵, R¹⁹, R²⁰, R²¹, R²², R²³, R²⁴ and    R²⁵ have the meanings given above.

A further form of stereoisomerism results from the cis-attachment of thetwo carbacyclic five-membered rings. Depending on the spatialarrangement of the grouping Q-Y or R⁵, two different spatial isomers areformed.

Hereinbelow, these isomers are referred to as “syn” and “anti”,respectively, depending on whether the grouping Q-Y in the compoundsaccording to the invention is in the anti- or syn-position to thecyclopentanedione ring. For example, if R⁵ is hydrogen, Q is a —CH₂—group, Y is —CO₂CH₃ and R¹, R², R³ and R⁴ have the meaning given in theformula (I-a), syn- and anti-isomers are defined as follows:

Furthermore, it has been found that the novel compounds of the formula(I) are obtained by one of the processes described below:

-   (A) Compounds of the formula (I-a)

-   -   in which    -   Q, Y, R¹, R², R³, R⁴ and R⁵ have the meaning given above    -   are obtained when    -   ketocarboxylic esters of the formula (II)

-   -   in which    -   Q, Y, R¹, R², R³, R⁴ and R⁵ have the meaning given above and    -   R²⁶ represents alkyl (in particular C₁-C₈-alkyl)    -   are cyclized intramolecularly, if appropriate in the presence of        a diluent in the presence of a base.

Compounds of the formula (I-a) are furthermore obtained by furtherfunctionalization of compounds which are already known, for example thesynthesis examples I-a-4 and I-a-5 from WO2010/040460, the preparationof which is known from the literature.

The synthetic transformation of these substances and analogoussubstances into the compounds of the formula (I) according to theinvention can be carried out by known standard processes of organicchemistry familiar to the person skilled in the art, for examplehydroboration, alkylation, acylation, oxidation, reduction,acetalization, condensation, Wittig reaction, Grignard or organometaladdition, halogenation or nucleophilic substitution reactions. Some ofthese processes are outlined in an exemplary manner in schemes 1 and 2.Further details can additionally also be found in the preparationexamples shown.

If the substituent G represents methyl, ethyl or benzyl, the substituentG is introduced by alkylation or benzylation starting with the compoundin which G represents hydrogen.

Moreover, it has been found

-   (B) that the compounds of the formula (I-b) shown above in which G,    Q, Y, R¹, R², R³, R⁴ and R⁵ have the meaning given above are    obtained when compounds of the formula (I-a) shown above in which Q,    Y, R¹, R², R³, R⁴ and R⁵ have the meaning given above are in each    case reacted-   (α) with acid halides of the formula (III)

-   -   in which    -   R¹⁹ has the meaning given above and    -   Hal represents halogen (in particular chlorine or bromine)    -   or

-   (β) with carboxylic anhydrides of the formula (IV)    R¹⁹—CO—O—CO—R¹⁹  (IV)    -   in which    -   R¹⁹ has the meaning given above,    -   if appropriate in the presence of a diluent and if appropriate        in the presence of an acid binder;

-   (C) that the compounds of the formula (I-c) shown above in which Q,    Y, R¹, R², R³, R⁴ and R⁵ have the meaning given above and L    represents oxygen are obtained when the compounds of the formula    (I-a) shown above in which Q, Y, R¹, R², R³, R⁴ and R⁵ have the    meaning given above are in each case reacted    -   with chloroformic esters or chloroformic thio esters of the        formula (V)        R²⁰-M-CO—Cl  (V)    -   in which    -   R²⁰ and M have the meanings given above,    -   if appropriate in the presence of a diluent and if appropriate        in the presence of an acid binder;

-   (D) that compounds of the formula (I-c) shown above in which Q, Y,    R¹, R², R³, R⁴ and R⁵ have the meaning given above and L represents    sulphur are obtained when compounds of the formula (I-a) shown above    in which Q, Y, R¹, R², R³, R⁴ and R⁵ have the meaning given above    are in each case reacted    -   with chloromonothioformic esters or chlordithioformic esters of        the formula (VI)

-   -   in which    -   M and R²⁰ have the meanings given above,    -   if appropriate in the presence of a diluent and if appropriate        in the presence of an acid binder;

-   (E) that compounds of the formula (I-d) shown above in which Q, Y,    R¹, R², R³, R⁴ and R⁵ have the meaning given above are obtained when    compounds of the formula (I-a) shown above in which Q, Y, R¹, R²,    R³, R⁴ and R⁵ have the meaning given above are in each case reacted    -   with sulphonyl chlorides of the formula (VII)        R²¹—SO₂—Cl  (VII)    -   in which    -   R²¹ has the meaning given above,    -   if appropriate in the presence of a diluent and if appropriate        in the presence of an acid binder,

-   (F) that compounds of the formula (I-e) shown above in which Q, Y,    R¹, R², R³, R⁴ and R⁵ have the meaning given above are obtained when    compounds of the formula (I-a) shown above in which Q, Y, R¹, R²,    R³, R⁴ and R⁵ have the meaning given above are in each case reacted    -   with phosphorus compounds of the formula (VIII)

-   -   in which    -   L, R²² and R²³ have the meanings given above and    -   Hal represents halogen (in particular chlorine or bromine),    -   if appropriate in the presence of a diluent and if appropriate        in the presence of an acid binder,

-   (G) that compounds of the formula (I-f) shown above in which Q, Y,    R¹, R², R³, R⁴ and R⁵ have the meaning given above are obtained when    compounds of the formula (I-a) in which Q, Y, R¹, R², R³, R⁴ and R⁵    have the meaning given above are in each case reacted    -   with metal compounds or amines of the formulae (IX) or (X),        respectively

-   -   in which    -   Met represents a mono- or divalent metal (preferably an alkali        metal or alkaline earth metal, such as lithium, sodium,        potassium, magnesium or calcium),    -   t represents the number 1 or 2 and    -   R²⁷, R²⁸, R²⁹ and R³⁰ independently of one another represent        hydrogen or alkyl (preferably C₁-C₈-alkyl),    -   if appropriate in the presence of a diluent,

-   (H) that compounds of the formula (I-g) shown above in which Q, Y,    R¹, R², R³, R⁴, R⁵ and R²⁴ have the meaning given above and R²⁵ is    hydrogen are obtained    -   when compounds of the formula (I-a) shown above in which Q, Y,        R¹, R², R³, R⁴ and R⁵ have the meaning given above are in each        case reacted

-   (α) with isocyanates or isothiocyanates of the formula (XI)    R²⁴—N═C=L  (XI)    -   in which    -   R²⁴ and L have the meanings given above,    -   if appropriate in the presence of a diluent and if appropriate        in the presence of a catalyst, or

-   (β) with carbamoyl chlorides or thiocarbamoyl chlorides of the    formula (XII)

-   -   in which    -   L, R²⁴ and R²⁵ have the meanings given above,    -   if appropriate in the presence of a diluent and if appropriate        in the presence of an acid binder.

Furthermore, it has been found that the novel compounds of the formula(I) are very effective as pesticides, preferably as insecticides,acaricides and/or as herbicides.

The formula (I) provides a general definition of the compounds accordingto the invention. Preferred substituents or ranges of the radicals givenin the formulae mentioned above and below are illustrated below:

Preference is given to compounds of the formula (I) in which

if

-   Q represents a bond, a C₁-C₃-alkylene, a C₂-C₃-alkenylene or a    C₂-C₃-alkynylene chain,    then-   Y represents the groups —OR⁶, —S(O)_(p)R⁶, —CO₂R⁷, —CH═CH₂, cyano,    —SCN, —CONR⁸R⁹, —SO₂NR⁸R⁹, CR¹⁰═O, —NR¹¹R¹², —CR¹⁰═N—OR¹³,    —CR¹⁰═N—R¹⁴, CR¹⁰═N—NR¹⁵R¹⁶, —CR¹⁰(OR¹⁷OR¹⁸), —CR¹⁰(SR¹⁷OR¹⁸),    —CR¹⁰(SR¹⁷SR¹⁸), —CR¹⁰(NHR¹⁷NHR¹⁸), —CR¹⁰(NHR¹⁷OR¹⁸),    —CR¹⁰(NHR¹⁷SR¹⁸), —CH(CN)₂, —CH(OH)R⁶, halogen, —O(C=M)R¹⁰,    —S(C=M)R¹⁰, —O(C=M)NR¹¹R¹², —S(C=M)NR¹¹R¹², —NH(C=M)NR¹¹R¹²,    —O(C=M)OR⁷, —S(C=M)OR⁷, —NH(C=M)OR⁷ or represents the group W,-   or Q, Y and R⁵ together form one of the groups CHCN═,    CH(CO₂C₁-C₆-alkyl)=,

-   W represents one of the 3- to 7-membered saturated or partially    saturated heterocycles listed below, which may be attached in    various ways and may be mono- or polysubstituted by identical or    different substituents from the group consisting of R³¹ and R³²

-   G represents hydrogen, methyl, ethyl or benzyl (a) or represents one    of the groups

-   -   E represents a metal ion equivalent, a tertiary sulphonium ion        or an ammonium ion,    -   L represents oxygen or sulphur,    -   M represents oxygen or sulphur,

-   R¹ represents hydrogen, halogen, C₁-C₄-alkyl, halo-C₁-C₄-alkyl,    C₃-C₆-cycloalkyl, halo-C₃-C₆-cycloalkyl, C₂-C₄-alkenyl,    halo-C₂-C₄-alkenyl, C₂-C₄-alkynyl, halo-C₂-C₄-alkynyl, C₁-C₄-alkoxy,    halo-C₁-C₄-alkoxy, C₂-C₄-alkynyloxy, halo-C₂-C₄-alkynyloxy,    C₂-C₄-alkenyloxy, halo-C₂-C₄-alkenyloxy, C₁-C₃-alkylthio,    C₁-C₃-alkylsulphinyl, C₁-C₃-alkylsulphonyl, halo-C₁-C₃-alkylthio,    halo-C₁-C₃-alkylsulphinyl or halo-C₁-C₃-alkylsulphonyl,

-   R² and R³ independently of one another are identical or different    and represent hydrogen, halogen, C₁-C₄-alkyl, halo-C₁-C₄-alkyl,    C₂-C₄-alkenyl, halo-C₂-C₄-alkenyl, C₂-C₄-alkynyl,    halo-C₂-C₄-alkynyl, C₁-C₄-alkoxy, halo-C₁-C₄-alkoxy,    C₃-C₆-cycloalkyl, C₃-C₆-cycloalkoxy, halo-C₃-C₆-cycloalkoxy,    C₂-C₄-alkynyloxy, halo-C₂-C₄-alkynyloxy, C₂-C₄-alkenyloxy,    halo-C₂-C₄-alkenyloxy, C₁-C₃-alkylthio, C₁-C₃-alkylsulphinyl,    C₁-C₃-alkylsulphonyl, halo-C₁-C₃-alkylthio,    halo-C₁-C₃-alkylsulphinyl, halo-C₁-C₃-alkylsulphonyl, phenyl or    phenyl which is optionally mono- or polysubstituted by identical or    different substituents from the group consisting of halogen,    C₁-C₄-alkyl, halo-C₁-C₄-alkyl,

-   R⁴ represents hydrogen, halogen, C₁-C₄-alkyl, halo-C₁-C₄-alkyl,    C₃-C₆-cycloalkyl, halo-C₃-C₆-cycloalkyl, C₁-C₄-alkoxy,    halo-C₁-C₄-alkoxy, C₃-C₄-cycloalkoxy, or halo-C₃-C₆-cycloalkoxy,

-   R⁵ represents hydrogen or C₁-C₄-alkyl,

-   R⁶ represents hydrogen, C₁-C₄-alkyl, halo-C₁-C₄-alkyl,    C₃-C₆-cycloalkyl, halo-C₃-C₆-cycloalkyl, C₂-C₄-alkenyl,    halo-C₂-C₄-alkenyl, C₂-C₄-alkynyl, halo-C₂-C₄-alkynyl,    C₁-C₄-alkoxy-C₁-C₄-alkyl, halo-C₁-C₄-alkoxy-C₁-C₄-alkyl,    C₃-C₆-cycloalkoxy-C₁-C₄-alkyl, halo-C₃-C₄-cycloalkoxy-C₁-C₄-alkyl,    represents benzyl, phenyl, heteroaryl, —CH₂-heteroaryl,    —CH₂CH₂-heteroaryl, (for example pyranyl, tetrahydrofuranyl,    pyrazolyl, thiazolyl, pyridyl, pyrimidyl, furanyl, thienyl,    benzoxazolyl, oxazolyl), C₁-C₄-alkanoyl, halo-C₁-C₄-alkanoyl,    benzoyl, each of which is optionally mono- or polysubstituted by    identical or different substituents from the group consisting of    halogen, cyano, nitro, C₁-C₄-alkyl, halo-C₁-C₄-alkyl,    C₃-C₆-cycloalkyl, halo-C₃-C₆-cycloalkyl, halo-C₂-C₄-alkenyl,    C₂-C₄-alkynyl, halo-C₂-C₄-alkynyl, C₁-C₄-alkoxyalkyl,    halo-C₁-C₄-alkoxy-C₁-C₆-alkyl, C₃-C₆-cycloalkoxy-C₁-C₆-alkyl and    halo-C₃-C₆-cycloalkoxy-C₁-C₆-alkyl, or represents benzoyl which is    optionally mono- or polysubstituted by identical or different    substituents from the group consisting of halogen, cyano, nitro,    C₁-C₄-alkyl, halo-C₁-C₄-alkyl, C₃-C₆-cycloalkyl and    halo-C₃-C₆-cycloalkyl,

-   R⁷ represents hydrogen, represents C₁-C₄-alkyl, C₃-C₆-cycloalkyl,    C₂-C₄-alkenyl, each of which is optionally mono- or polysubstituted    by identical or different substituents from the group consisting of    halogen and C₁-C₄-alkoxy, or represents a cation E,

-   R⁸ and R⁹ independently of one another are identical or different    and represent hydrogen, C₁-C₄-alkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl,    C₃-C₆-cycloalkyl, phenyl, benzyl, represent phenyl or benzyl, each    of which is mono- or polysubstituted by identical or different    substituents from the group consisting of halogen, nitro, cyano and    C₁-C₃-alkyl or

-   R⁸ and R⁹ together with the adjacent nitrogen atom form a    morpholino, piperidino or pyrrolidino group,

-   R¹⁰ represents hydrogen, C₁-C₄-alkyl, halo-C₁-C₄ alkyl,    C₂-C₄-alkenyl, halo-C₂-C₄-alkenyl, C₂-C₄-alkynyl, C₃-C₆-cycloalkyl,    represents phenyl or benzyl, each of which is optionally mono- or    polysubstituted by identical or different substituents from the    group consisting of halogen, C₁-C₄-alkyl and halo-C₁-C₄-alkyl,

-   R¹¹ and R¹² independently of one another are identical or different    and represent hydrogen, C₁-C₄-alkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl,    C₃-C₆-cycloalkyl, phenyl, benzyl, represent phenyl or benzyl, each    of which is mono- or polysubstituted by identical or different    substituents from the group consisting of halogen and C₁-C₃-alkyl or

-   R¹¹ and R¹² together with the adjacent nitrogen atom form a    morpholino, piperidino or pyrrolidino group,

-   R¹³ represents hydrogen or represents C₁-C₄-alkyl, C₂-C₄-alkenyl,    C₂-C₄-alkynyl, C₃-C₄-cycloalkyl, C₃-C₆-cycloalkyl-C₁-C₃-alkyl, each    of which is optionally mono- or polysubstituted by halogen,    represents benzyl or —CH₂-heterocyclyl, each of which is optionally    mono- or polysubstituted by identical or different substituents from    the group consisting of halogen and C₁-C₃-alkyl,

-   R¹⁴ represents hydrogen, C₁-C₄-alkyl, halo-C₁-C₄ alkyl,    C₂-C₄-alkenyl, C₂-C₄-alkynyl, halo-C₂-C₄-alkynyl, phenyl, benzyl or    represents phenyl or benzyl, each of which is mono- or    polysubstituted by identical or different substituents from the    group consisting of halogen, C₁-C₃-alkyl, halo-C₁-C₃-alkyl,    C₃-C₆-cycloalkyl, halo-C₃-C₆-cycloalkyl,

-   R¹⁵ and R¹⁶ independently of one another are identical or different    and represent hydrogen, C₁-C₄-alkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl,    C₃-C₆-cycloalkyl, phenyl, benzyl, represent phenyl or benzyl, each    of which is mono- or polysubstituted by identical or different    substituents from the group consisting of halogen and C₁-C₃-alkyl or

-   R¹⁵ and R¹⁶ together with the adjacent nitrogen atom form a    morpholino, piperidino or pyrrolidino group,

-   R¹⁷ represents hydrogen, represents C₁-C₄-alkyl, benzyl or    halo-C₁-C₄-alkyl, each of which is optionally interrupted once or    more by identical or different radicals from the group consisting of    oxygen and sulphur,

-   R¹⁸ represents hydrogen, represents C₁-C₄-alkyl, benzyl or    halo-C₁-C₄-alkyl, each of which is optionally interrupted once or    more by identical or different radicals from the group consisting of    oxygen and sulphur,

-   R¹⁹ represents optionally halogen-substituted C₁-C₆-alkyl,    C₂-C₆-alkenyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,    C₁-C₃-alkylthio-C₁-C₄-alkyl, poly-C₁-C₄-alkoxy-C₁-C₄-alkyl or    represents C₃-C₆-cycloalkyl which is optionally mono- or    polysubstituted by identical or different substituents from the    group consisting of halogen, C₁-C₄-alkyl and C₁-C₄-alkoxy and in    which optionally one or more (preferably not more than two) not    directly adjacent ring members are replaced by oxygen and/or    sulphur, represents in each case optionally halogen- or    C₁-C₄-alkyl-substituted phenyl, phenyl-C₁-C₄-alkyl, hetaryl (for    example pyrazolyl, thiazolyl, pyridyl, pyrimidyl, furanyl or    thienyl), phenoxy-C₁-C₄-alkyl or hetaryloxy-C₁-C₄-alkyl (for example    pyridyloxy-C₁-C₄-alkyl, pyrimidyloxy-C₁-C₄-alkyl or    thiazolyloxy-C₁-C₄-alkyl),

-   R²⁰ represents C₁-C₆-alkyl, C₂-C₆-alkenyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,    poly-C₁-C₄-alkoxy-C₁-C₄-alkyl, each of which is optionally mono- or    polysubstituted by identical or different halogen, or represents    C₃-C₆-cycloalkyl in which optionally one or more (preferably not    more than two) not directly adjacent ring members are replaced by    oxygen and/or sulphur, or represents benzyl,

-   R²¹, R²² and R²³ independently of one another are identical or    different and represent C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-alkylamino,    C₁-C₄-dialkylamino, C₁-C₃-alkylthio, C₂-C₄-alkenylthio,    C₃-C₆-cycloalkylthio, each of which is optionally mono- or    polysubstituted by identical or different halogen, or represent    phenyl, benzyl, phenoxy or phenylthio, each of which is optionally    mono- or polysubstituted by identical or different substituents from    the group consisting of halogen, C₁-C₆-alkyl, C₁-C₆-alkoxy,    C₁-C₄-haloalkyl, C₁-C₄-haloalkoxy, cyano and nitro,

-   R²⁴ and R²⁵ independently of one another are identical or different    and represent hydrogen, represent C₁-C₆-alkyl, C₃-C₆-cycloalkyl,    C₂-C₆-alkenyl, C₁-C₆-alkoxy, C₁-C₆-alkoxy-C₁-C₄-alkyl, each of which    is optionally mono- or polysubstituted by identical or different    halogen, represent benzyl or phenyl, optionally mono- or    polysubstituted by identical or different substituents from the    group consisting of halogen and C₁-C₄-alkyl or

-   R²⁴ and R²⁵ together with the adjacent nitrogen atom form a    morpholino, piperidino or pyrrolidino group,

-   R³¹ represents halogen, cyano, nitro, C₁-C₆-alkyl, halo-C₁-C₆-alkyl,    C₃-C₆-cycloalkyl, halo-C₃-C₆-cycloalkyl, C₂-C₆-alkenyl,    halo-C₂-C₆-alkenyl, C₂-C₆-alkynyl, halo-C₂-C₆-alkynyl, C₁-C₆-alkoxy,    halo-C₁-C₆-alkoxy, C₃-C₆-cycloalkoxy, halo-C₃-C₆-cycloalkoxy,    C₁-C₆-alkynyloxy, halo-C₁-C₆-alkynyloxy, C₂-C₆-alkenyloxy,    halo-C₂-C₆-alkenyloxy, C₁-C₃-alkylthio, C₁-C₃-alkylsulphinyl,    C₁-C₃-alkylsulphonyl, halo-C₁-C₃-alkylthio,    halo-C₁-C₃-alkylsulphinyl, C₁-C₃-alkylsulphonyl,    C₁-C₆-alkylcarbonyl, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylcarbamoyl,    amino, C₁-C₆-alkylamino or C₁-C₆-dialkylamino,

-   R³² represents hydrogen, halogen, cyano, nitro, C₁-C₆-alkyl,    halo-C₁-C₆-alkyl, C₃-C₆-cycloalkyl, halo-C₃-C₆-cycloalkyl,    C₂-C₆-alkenyl, halo-C₂-C₆-alkenyl, C₂-C₆-alkynyl,    halo-C₂-C₆-alkynyl, C₁-C₃-alkylsulphonyl, C₁-C₃-alkylsulphonyl,    C₁-C₆-alkylcarbonyl, C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylcarbamoyl,    amino, C₁-C₆-alkylamino or C₁-C₆-dialkylamino,

-   n represents the number 0, 1, 2, 3, 4, 5 or 6,

-   P represents the number 0, 1 or 2,    or if

-   Q, Y and R⁵ together represent the group CH₂═, then

-   G represents methyl, ethyl or benzyl (a).

Particular preference is given to compounds of the formula (I) in which

if

-   Q represents a bond, —CH₂—, —CH═CH— or —CH₂CH₂—,    then-   Y represents the groups —OR⁶, —CO₂R⁷, —CH═CH₂, cyano, —CR¹⁰═O,    —CR¹⁰═N—OR¹³, —CH(OR¹⁷OR¹⁸), S(O)_(p)R⁶, —SCN, —CONR⁸R⁹, —CH(CN)₂,    —CH(OH)R⁶, halogen, —OC=MR¹⁰, —S(C=M)R¹⁰, —O(C=M)NR¹¹R¹²,    —O(C=M)OR⁷, —NH(C=M)OR⁷, or represents the group W,-   or Q, Y and R⁵ together form one of the groups

-   W represents

-   G represents hydrogen, ethyl or benzyl or represents one of the    groups

-   R¹ represents methyl, ethyl, methoxy, ethoxy, halogen or    cyclopropyl,-   R² represents methyl, ethyl or 4-chlorophenyl,-   R³ represents hydrogen, methyl, ethyl or cyclopropyl,-   R⁴ represents hydrogen, methyl or ethyl,-   R⁵ represents hydrogen,-   R⁶ represents hydrogen, methyl, ethyl, —CH₂—CH(CH₃)₂, —CH₂—CH═CH₂,    cyano, trifluoromethyl, methoxymethyl, 2-benzoxazolyl,    4,5-dimethylthiazol-2-yl, 2-oxazolyl, 2-tetrahydrofuryl or the    2-pyranyl group,-   R⁷ represents hydrogen, methyl, ethyl, isopropyl or n-propyl,-   R⁸ represents hydrogen or methyl,-   R⁹ represents hydrogen or methyl,-   or R⁸ and R⁹ together with the nitrogen atom form the group

-   R¹⁰ represents hydrogen, methyl, t-butyl, fluoromethyl,    difluoromethyl or trifluoromethyl,-   R¹¹ represents hydrogen or methyl,-   R¹² represents hydrogen, methyl, benzyl or phenyl,-   R¹³ represents hydrogen, methyl, isopropyl, —CH₂CH═CCl₂, —CH₂CH═CH₂,    —CH₂C≡CH or —CH₂C₃H₅,-   R¹⁷ represents methyl, ethyl or n-propyl-   R¹⁸ represents methyl, ethyl or n-propyl,-   R¹⁹ represents C₁-C₄-alkyl-   R²⁰ represents methyl, ethyl or isopropyl,-   p represents 0 or 2,-   M represents oxygen or sulphur,    or if-   Q, Y and R⁵ together represent the group CH₂═,    then-   G represents methyl, ethyl or benzyl (a).

Very particular preference is given to compounds of the formula (I) inwhich

-   Q represents a bond, —CH₂—, —CH₂CH₂— or —CH═CH—,-   Y represents the groups —OR⁶, —CO₂R⁷, —CH═CH₂, cyano, —CR¹⁰═O,    —CR¹⁰═N—OR¹³, —CH(OR¹⁷OR¹⁸), S(O)_(p)R⁶, —SCN, —CONR⁸R⁹, —CH(CN)₂,    —CH(OH)R⁶, bromine, —O(C═O)R¹⁰, —S(C═P)R¹⁰, —O(C═O)NR¹¹R¹², or    represents the group W,-   or Q, Y and R⁵ together form one of the groups

-   W represents

-   G represents hydrogen, ethyl, benzyl (a) or represents one of the    groups

-   R¹ represents methyl or ethyl (ethyl is especially preferred),-   R² represents methyl,-   R³ represents hydrogen,-   R⁴ represents methyl or ethyl (ethyl is especially preferred),-   R⁵ represents hydrogen,-   R⁶ represents hydrogen, methyl, ethyl, —CH₂—CH(CH₃)₂, —CH₂—CH═CH₂,    trifluoromethyl, methoxymethyl, 2-benzoxazolyl,    4,5-dimethylthiazol-2-yl, 2-oxazolyl, 2-tetrahydrofuryl or the    2-pyranyl group,-   R⁷ represents hydrogen, methyl or ethyl,-   R⁸ represents hydrogen or methyl,-   R⁹ represents hydrogen or methyl,-   or R⁸ and R⁹ together with the nitrogen atom represent the group

-   R¹⁰ represents hydrogen, methyl, t-butyl or trifluoromethyl,-   R¹¹ represents hydrogen or methyl,-   R¹² represents hydrogen, methyl, benzyl or phenyl,-   R¹³ represents hydrogen, methyl, isopropyl, —CH₂CH═CCl₂, —CH₂CH═CH₂,    —CH₂C≡CH or —CH₂C₃H₅,-   R¹⁷ represents methyl or ethyl,-   R¹⁸ represents methyl or ethyl,-   R¹⁹ represents ethyl, tert-butyl or isopropyl,-   R²⁰ represents methyl, ethyl or isopropyl,-   p represents 0 or 2.

Emphasis is given to compounds of the formula (I) in which

-   Q, Y and R⁵ together represent the group CH₂═,-   G represents benzyl (a),-   R¹ represents ethyl,-   R² represents methyl,-   R³ represents hydrogen,-   R⁴ represents ethyl.

The general or preferred radical definitions or illustrations listedabove can be combined with one another as desired, i.e. includingcombinations between the respective ranges and preferred ranges. Theyapply both to the end products and, correspondingly, to the precursorsand intermediates.

Preference according to the invention is given to the compounds of theformula (I) which contain a combination of the meanings listed above asbeing preferred (preferable).

Particular preference according to the invention is given to thecompounds of the formula (I) which contain a combination of the meaningslisted above as being particularly preferred.

Very particular preference according to the invention is given to thecompounds of the formula (I) which contain a combination of the meaningslisted above as being very particularly preferred.

Emphasis according to the invention is given to the compounds of theformula (I) which contain a combination of the meanings listed above asemphasized.

Special preference according to the invention is given to the compoundsof the formula (I) which contain a combination of the meanings listedabove as being especially preferred.

Saturated or unsaturated hydrocarbon radicals, such as alkyl, alkanediylor alkenyl, can in each case be straight-chain or branched as far asthis is possible, including in combination with heteroatoms, such as,for example, in alkoxy.

Optionally substituted radicals may be mono- or polysubstituted unlessindicated otherwise, and in the case of multiple substitutions thesubstituents can be identical or different.

With particular emphasis, G represents hydrogen.

In addition to the compounds mentioned in the Preparation Examples, thefollowing compounds of the formula (I-1-a) may be specificallymentioned:

TABLE 1 R¹ = CH₃, R² = CH₃, R³ = CH_(3,) R⁴ = H, R⁵ = H, Y Q —CO₂H bond—CO₂Me bond —CO₂Et bond —CO₂ ^(i)Pr bond —CONH₂ bond —CONHCH₃ bond—CON(CH₃)₂ bond

bond —CN bond —SCN bond —CHO bond —CH═N—OH bond —CH═N—OCH₃ bond—CH═N—O—CH₂C═CH₂ bond —CH═N—O—CH₂C═CCl₃ bond —CH═N—O—CH₂C≡CH bond—CH═N—O^(i)Pr bond CH₃(C═O)— bond

bond —CH═CH₃ bond —CH(CN)₃ bond —C(CN)(CO₂CH₃) bond —C(CO₂CH₃)₂ bond

bond

bond

bond

bond

bond

bond

bond

bond

bond

bond

bond

bond

bond —OH —CH₂— —OCH₃ —CH₂— —OCF₂ —CH₂— —OCHF₂ —CH₂— —OCH₂F —CH₂——OCH₂CH₃ —CH₂— —OCH₂OCH₃ —CH₂—

—CH₂—

—CH₂—

—CH₂— —O(C═O)—OCH₃ —CH₂— —O(C═O)—OCF₃ —CH₂— —O(C═O)—OC₂H₅ —CH₂——O(C═O)—N(CH₃)₂ —CH₂— —O(C═O)—NHC₆H₅ —CH₂— —O(C═O)—NHCH₂C₆H₅ —CH₂——O(C═O)—NHCH₃ —CH₂— —O(C═S)—NHC₆H₅ —CH₂— —CHO —CH₂— —CO₂H —CH₂— —CO₂Me—CH₂— —CO₂Et —CH₂— —CO₂ ^(i)Pr —CH₂— —CONH₂ —CH₂— —CONHCH₃ —CH₂——CON(CH₃)₂ —CH₂—

—CH₂—

—CH₂—

—CH₂—

—CH₂—

—CH₂—

—CH₂—

—CH₂—

—CH₂—

—CH₂—

—CH₂—

—CH₂—

—CH₂—

—CH₂—

—CH₂—

—CH₂—

—CH₂—

—CH₂— —CN —CH₂— —Cl —CH₂— —Br —CH₂— —SCN —CH₂— —CH═N—OH —CH₂— —CH═N—OCH₃—CH₂— —CH═N—O—CH₂C═CH₂ —CH₂— —CH═N—O—CH₂C═CCl₃ —CH₂— —CH═N—O—CH₂C≡CH—CH₂— —CH═N—O^(i)Pr —CH₂—

—CH₂— —SCH₂CH═CH₂ —CH₂— —SCH₃ —CH₂— —SO₂CH₃ —CH₂— CH₃(C═O)S— —CH₂—(CH₃)₂CHCH₂SO₂— —CH₂— (CH₃)₂CHCH₂S— —CH₂—

—CH₂—

—CH₂—

—CH₂— —OCH₂CH₃ —CH═CH— —O(C═O)—OCH₃ —CH═CH— —O(C═O)—OC₂H₅ —CH═CH——O(C═O)—N(CH₃)₂ —CH═CH— —O(C═O)—NHC₆H₅ —CH═CH— —O(C═O)—NHCH₃ —CH═CH——O(C═S)—NHC₆H₅ —CH═CH— —CO₂H —CH═CH— —CO₂Me —CH═CH— —CO₂Et —CH═CH— —CO₂^(i)Pr —CH═CH— —CONH₂ —CH═CH—

—CH═CH—

—CH═CH—

—CH═CH—

—CH═CH—

—CH═CH—

—CH═CH—

—CH═CH—

—CH═CH—

—CH═CH—

—CH═CH—

—CH═CH—

—CH═CH—

—CH═CH—

—CH═CH—

—CH═CH—

—CH═CH—

—CH═CH— —CN —CH₂CH₂— CH₃(C═O)— —CH₂CH₂—

—CH₂CH₂— —CHO —CH₂CH₂— —OCH₃ —CH₂CH₂— —OCH₂CH₃ —CH₂CH₂— —O(C═O)—OCH₃—CH₂CH₂— —O(C═O)—OC₂H₅ —CH₂CH₂— —O(C═O)—N(CH₃)₂ —CH₂CH₂— —O(C═O)—NHC₆H₅—CH₂CH₂— —O(C═O)—NHCH₃ —CH₂CH₂— —O(C═S)—NHC₆H₅ —CH₂CH₂— —CO₂H —CH₂CH₂——CO₂Me —CH₂CH₂— —CO₂Et —CH₂CH₂— —CO₂ ^(i)Pr —CH₂CH₂— —CONH₂ —CH₂CH₂—

—CH₂CH₂—

—CH₂CH₂—

—CH₂CH₂—

—CH₂CH₂—

—CH₂CH₂—

—CH₂CH₂—

—CH₂CH₂—

—CH₂CH₂—

—CH₂CH₂—

—CH₂CH₂—

—CH₂CH₂—

—CH₂CH₂—

—CH₂CH₂—

—CH₂CH₂—

—CH₂CH₂—

—CH₂CH₂—

—CH₂CH₂—Table 2: Q and Y as mentioned in Table 1 and

-   -   R¹=C₂H₅, R²=CH₃, R³=CH₃, R⁴=H, R⁵=H,        Table 3: Q and Y as mentioned in Table 1 and    -   R¹=C₂H₅, R²=CH₃, R³=C₂H₅, R⁴=H, R⁵=H,        Table 4: Q and Y as mentioned in Table 1 and    -   R¹=C₂H₅; R²=C₂H₅; R³=C₂H₅, R⁴=H, R⁵=H,        Table 5: Q and Y as mentioned in Table 1 and    -   R¹=        ; R²=CH₃; R³=CH₃; R⁴=H, R⁵=H,        Table 6: Q and Y as mentioned in Table 1 and    -   R¹=        ; R²=CH₃; R³=C₂H₅, R⁴=H, R⁵=H,        Table 7: Q and Y as mentioned in Table 1 and    -   R¹=OCH₃; R²=CH₃; R³=CH₃, R⁴=H, R⁵=H,        Table 8: Q and Y as mentioned in Table 1 and    -   R¹=OC₂H₅; R²=CH₃; R³=CH₃, R⁴=H, R⁵=H,        Table 9: Q and Y as mentioned in Table 1 and    -   R¹=OCH₃; R²=CH₃; R³=C₂H₅, R⁴=H, R⁵=H,        Table 10: Q and Y as mentioned in Table 1 and    -   R¹=OC₂H₅; R²=CH₃; R³=C₂H₅, R⁴=H, R⁵=H,        Table 11: Q and Y as mentioned in Table 1 and    -   R¹=C₂H₅; R²=CH₃; R³=H, R⁴=H, R⁵=H,        Table 12: Q and Y as mentioned in Table 1 and    -   R¹=        R²=CH₃; R³=        , R⁴=H, R⁵=H,        Table 13: Q and Y as mentioned in Table 1 and    -   R¹=C₂H₅; R²=C₂H₅; R³=CH₃, R⁴=H, R⁵=H,        Table 14: Q and Y as mentioned in Table 1 and    -   R¹=CH₃; R²=4-chlorophenyl; R³=H, R⁴=CH₃, R⁵=H.

Surprisingly, it has now also been found that the compounds of theformula (I), when used together with the crop plantcompatibility-improving compounds (safener/antidotes) described below,efficiently prevent damage to the crop plants and can be used in aparticularly advantageous manner as broad-spectrum combinationpreparations for the selective control of unwanted plants in crops ofuseful plants, such as, for example, in cereals, but also in maize, soyabeans and rice.

The invention also provides selective herbicidal compositions comprisingan effective amount of an active compound combination comprising, ascomponents,

-   a′) at least one compound of the formula (I), in which R¹, R², R³,    R⁴, R⁵, Y, Q and G have the meaning given above    and-   (b′) at least one crop plant compatibility-improving compound    (safener).

Suitable safeners are, for example, the following groups of compounds:

-   -   S1) Compounds of the formula (S1)

-   -   where the symbols and indices have the following meanings:    -   n_(A) is a natural number from 0 to 5, preferably from 0 to 3;    -   R_(A) ¹ is halogen, (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy, nitro or        (C₁-C₄)-haloalkyl;    -   W_(A) is an unsubstituted or substituted divalent heterocyclic        radical from the group consisting of partially unsaturated or        aromatic five-membered heterocycles having 1 to 3 hetero ring        atoms from the group consisting of N and O, where at least one        nitrogen atom and at most one oxygen atom is present in the        ring, preferably a radical from the group consisting of (W_(A)        ¹) to (W_(A) ⁴),

-   -   m_(A) is 0 or 1;    -   R_(A) ² is OR_(A) ³, SR_(A) ³ or NR_(A) ³R_(A) ⁴ or a saturated        or unsaturated 3- to 7-membered heterocycle having at least one        nitrogen atom and up to 3 heteroatoms, preferably from the group        consisting of O and S, which is attached via the nitrogen atom        to the carbonyl group in (S1) and which is unsubstituted or        substituted by radicals from the group consisting of        (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy and optionally substituted phenyl,        preferably a radical of the formula OR_(A) ³, NHR_(A) ⁴ or        N(CH₃)₂, in particular of the formula OR_(A) ³;    -   R_(A) ³ is hydrogen or an unsubstituted or substituted aliphatic        hydrocarbon radical having preferably a total of 1 to 18 carbon        atoms;    -   R⁴ is hydrogen, (C₁-C₆)-alkyl, (C₁-C₆)-alkoxy or substituted or        unsubstituted phenyl;    -   R_(A) ⁵ is H, (C₁-C₈)-alkyl, (C₁-C₈)-haloalkyl,        (C₁-C₄)-alkoxy-(C₁-C₈)-alkyl, cyano or COOR_(A) ⁹ where R_(A) ⁹        is hydrogen, (C₁-C₈)-alkyl, (C₁-C₈)-haloalkyl,        (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, (C₁-C₆)-hydroxyalkyl,        (C₃-C₁₂)-cycloalkyl or tri-(C₁-C₄)-alkylsilyl;    -   R_(A) ⁶, R_(A) ⁷, R_(A) ⁸ are identical or different and are        hydrogen, (C₁-C₈)-alkyl, (C₁-C₈)-haloalkyl, (C₃-C₁₂)-cycloalkyl        or substituted or unsubstituted phenyl;    -   preferably:    -   a) compounds of the type of the        dichlorophenylpyrazoline-3-carboxylic acid (S1^(a)), preferably        compounds such as        1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazoline-3-carboxylic        acid, ethyl        1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazoline-3-carboxylate        (S1-1) (“mefenpyr-diethyl”), and related compounds, as described        in WO-A-91/07874;    -   b) derivatives of dichlorophenylpyrazolecarboxylic acid        (S1^(b)), preferably compounds such as ethyl        1-(2,4-dichlorophenyl)-5-methylpyrazole-3-carboxylate (S1-2),        ethyl 1-(2,4-dichlorophenyl)-5-isopropylpyrazole-3-carboxylate        (S1-3), ethyl        1-(2,4-dichlorophenyl)-5-(1,1-dimethylethyl)pyrazole-3-carboxylate        (S1-4) and related compounds, as described in EP-A-333 131 and        EP-A-269 806;    -   c) derivatives of 1,5-diphenylpyrazole-3-carboxylic acid        (S1^(c)), preferably compounds such as ethyl        1-(2,4-dichlorophenyl)-5-phenylpyrazole-3-carboxylate (S1-5),        methyl 1-(2-chlorophenyl)-5-phenylpyrazole-3-carboxylate (S1-6)        and related compounds, as described, for example, in        EP-A-268554;    -   d) compounds of the type of the triazolecarboxylic acids        (S1^(d)), preferably compounds such as fenchlorazole(-ethyl),        i.e. ethyl        1-(2,4-dichlorophenyl)-5-trichloromethyl-(1H)-1,2,4-triazole-3-carboxylate        (S1-7), and related compounds, as described in EP-A-174 562 and        EP-A-346 620;    -   e) compounds of the type of the 5-benzyl- or        5-phenyl-2-isoxazoline-3-carboxylic acid or the        5,5-diphenyl-2-isoxazoline-3-carboxylic acid (S1^(e)),        preferably compounds such as ethyl        5-(2,4-dichlorobenzyl)-2-isoxazoline-3-carboxylate (S1-8) or        ethyl 5-phenyl-2-isoxazoline-3-carboxylate (S1-9) and related        compounds, as described in WO-A-91/08202, or        5,5-diphenyl-2-isoxazolinecarboxylic acid (S1-10) or ethyl        5,5-diphenyl-2-isoxazolinecarboxylate (S1-11)        (“isoxadifen-ethyl”) or n-propyl        5,5-diphenyl-2-isoxazolinecarboxylate (S1-12) or ethyl        5-(4-fluorophenyl)-5-phenyl-2-isoxazoline-3-carboxylate (S1-13),        as described in the patent application WO-A-95/07897.    -   S2) Quinoline derivatives of the formula (S2)

-   -   where the symbols and indices have the following meanings:    -   R_(B) ¹ is halogen, (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy, nitro or        (C₁-C₄)-haloalkyl;    -   n_(B) is a natural number from 0 to 5, preferably from 0 to 3;    -   R_(B) ² is OR_(B) ³, SR_(B) ³ or NR_(B) ³R_(B) ⁴ or a saturated        -   or unsaturated 3- to 7-membered heterocycle having at least            one nitrogen atom and up to 3 heteroatoms, preferably from            the group consisting of O and S, which is attached via the            nitrogen atom to the carbonyl group in (S2) and which is            unsubstituted or substituted by radicals from the group            consisting of (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy and optionally            substituted phenyl, preferably a radical of the formula            OR_(B) ³, NHR_(B) ⁴ or N(CH₃)₂, in particular of the formula            OR_(B) ³;    -   R_(B) ³ is hydrogen or an unsubstituted or substituted aliphatic        hydrocarbon radical having preferably a total of 1 to 18 carbon        atoms;    -   R_(B) ⁴ is hydrogen, (C₁-C₆)-alkyl, (C₁-C₆)-alkoxy or        substituted or unsubstituted phenyl;    -   T_(B) is a (C₁- or C₂)-alkanediyl chain which is unsubstituted        or substituted by one or two (C₁-C₄)-alkyl radicals or by        [(C₁-C₃)-alkoxy]carbonyl;    -   preferably:    -   a) compounds of the type of the 8-quinolinoxyacetic acid        (S2^(a)), preferably 1-methylhexyl        (5-chloro-8-quinolinoxy)acetate (“cloquintocet-mexyl”) (S2-1),        1,3-dimethyl-but-1-yl (5-chloro-8-quinolinoxy)acetate (S2-2),        4-allyloxybutyl (5-chloro-8-quinolinoxy)acetate (S2-3),        1-allyloxyprop-2-yl (5-chloro-8-quinolinoxy)acetate (S2-4),        ethyl (5-chloro-8-quinolinoxy)acetate (S2-5), methyl        (5-chloro-8-quinolinoxy)acetate (S2-6), allyl        (5-chloro-8-quinolinoxy)acetate (S2-7),        2-(2-propylideneiminoxy)-1-ethyl (5-chloro-8-quinolinoxy)acetate        (S2-8), 2-oxo-prop-1-yl (5-chloro-8-quinolinoxy)acetate (S2-9)        and related compounds, as described in EP-A-86 750, EP-A-94 349        and EP-A-191 736 or EP-A-0 492 366, and also        (5-chloro-8-quinolinoxy)acetic acid (S2-10), its hydrates and        salts, for example its lithium, sodium, potassium, calcium,        magnesium, aluminium, iron, ammonium, quaternary ammonium,        sulphonium or phosphonium salts, as described in        WO-A-2002/34048;    -   b) compounds of the type of the (5-chloro-8-quinolinoxy)malonic        acid (S2^(b)), preferably compounds such as diethyl        (5-chloro-8-quinolinoxy)malonate, diallyl        (5-chloro-8-quinolinoxy)malonate, methyl ethyl        (5-chloro-8-quinolinoxy)malonate and related compounds, as        described in EP-A-0 582 198.    -   S3) Compounds of the formula (S3)

-   -   where the symbols and indices have the following meanings:    -   R_(C) ¹ is (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₂-C₄)-alkenyl,        (C₂-C₄)-haloalkenyl, (C₃-C₇)-cycloalkyl, preferably        dichloromethyl;    -   R_(C) ², R_(C) ³ are identical or different and are hydrogen,        (C₁-C₄)-alkyl, (C₂-C₄)-alkenyl, (C₂-C₄)-alkynyl,        (C₁-C₄)-haloalkyl, (C₂-C₄)-haloalkenyl,        (C₁-C₄)-alkylcarbamoyl-(C₁-C₄)-alkyl,        (C₂-C₄)-alkenylcarbamoyl-(C₁-C₄)-alkyl,        (C₁-C₄)-alkoxy-(C₁-C₄)-alkyl, dioxolanyl-(C₁-C₄)-alkyl,        thiazolyl, furyl, furylalkyl, thienyl, piperidyl, substituted or        unsubstituted phenyl, or R_(C) ² and R_(C) ³ together form a        substituted or unsubstituted heterocyclic ring, preferably an        oxazolidine, thiazolidine, piperidine, morpholine,        hexahydropyrimidine or benzoxazine ring;    -   preferably:        -   active compounds of the type of the dichloroacetamides which            are frequently used as pre-emergence safeners (soil-acting            safeners), such as, for example,        -   “dichlormid” (N,N-diallyl-2,2-dichloroacetamide) (S3-1),        -   “R-29148” (3-dichloroacetyl-2,2,5-trimethyl-1,3-oxazolidine)            from Stauffer (S3-2),        -   “R-28725” (3-dichloroacetyl-2,2-dimethyl-1,3-oxazolidine)            from Stauffer (S3-3),        -   “benoxacor”            (4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine)            (S3-4),        -   “PPG-1292”            (N-allyl-N-[(1,3-dioxolan-2-yl)methyl]dichloroacetamide)            from PPG Industries (S3-5),        -   “DKA-24”            (N-allyl-N-[(allylaminocarbonyl)methyl]dichloroacetamide)            from Sagro-Chem (S3-6),        -   “AD-67” or “MON 4660”            (3-dichloroacetyl-1-oxa-3-azaspiro[4,5]decane) from            Nitrokemia or Monsanto (S3-7),        -   “TI-35” (1-dichloroacetylazepane) from TRI-Chemical RT            (S3-8)        -   “diclonon” (dicyclonon) or “BAS145138” or “LAB145138” (S3-9)            (3-dichloroacetyl-2,5,5-trimethyl-1,3-diazabicyclo[4.3.0]nonane)            from BASF,        -   “furilazole” or “MON 13900”            ((RS)-3-dichloroacetyl-5-(2-furyl)-2,2-dimethyloxazolidine)            (S3-10) and also its (R)-isomer (S3-11).    -   S4) N-Acylsulphonamides of the formula (S4) and their salts

-   -   where the symbols and indices have the following meanings:    -   X_(D) is CH or N;    -   R_(D) ¹ is CO—NR_(D) ⁵R_(D) ⁶ or NHCO—R_(D) ⁷;    -   R_(D) ² is halogen, (C₁-C₄)-haloalkyl, (C₁-C₄)-haloalkoxy,        nitro, (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-alkylsulphonyl,        (C₁-C₄)-alkoxycarbonyl or (C₁-C₄)-alkylcarbonyl;    -   R_(D) ³ is hydrogen, (C₁-C₄)-alkyl, (C₂-C₄)-alkenyl or        (C₂-C₄)-alkynyl;    -   R_(D) ⁴ is halogen, nitro, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl,        (C₁-C₄)-haloalkoxy, (C₃-C₆)-cycloalkyl, phenyl, (C₁-C₄)-alkoxy,        cyano, (C₁-C₄)-alkylthio, (C₁-C₄)-alkylsulphinyl,        (C₁-C₄)-alkylsulphonyl, (C₁-C₄)-alkoxycarbonyl or        (C₁-C₄)-alkylcarbonyl;    -   R_(D) ⁵ is hydrogen, (C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl,        (C₂-C₆)-alkenyl, (C₂-C₆)-alkynyl, (C₅-C₆)-cycloalkenyl, phenyl        or 3- to 6-membered heterocyclyl which contains v_(D)        heteroatoms from the group consisting of nitrogen, oxygen and        sulphur, where the seven last-mentioned radicals are substituted        by v_(D) substituents from the group consisting of halogen,        (C₁-C₆)-alkoxy, (C₁-C₆)-haloalkoxy, (C₁-C₂)-alkylsulphinyl,        (C₁-C₂)-alkylsulphonyl, (C₃-C₆)-cycloalkyl,        (C₁-C₄)-alkoxycarbonyl, (C₁-C₄)-alkylcarbonyl and phenyl and, in        the case of cyclic radicals, also (C₁-C₄)-alkyl and        (C₁-C₄)-haloalkyl;    -   R_(D) ⁶ is hydrogen, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl or        (C₂-C₆)-alkynyl, where the three last-mentioned radicals are        substituted by v_(D) radicals from the group consisting of        halogen, hydroxy, (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy and        (C₁-C₄)-alkylthio, or    -   R_(D) ⁵ and R_(D) ⁶ together with the nitrogen atom carrying        them form a pyrrolidinyl or piperidinyl radical;    -   R_(D) ⁷ is hydrogen, (C₁-C₄)-alkylamino, di-(C₁-C₄)-alkylamino,        (C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl, where the 2 last-mentioned        radicals are substituted by v_(D) substituents from the group        consisting of halogen, (C₁-C₄)-alkoxy, halo-(C₁-C₆)-alkoxy and        (C₁-C₄)-alkylthio and, in the case of cyclic radicals, also        (C₁-C₄)-alkyl and (C₁-C₄)-haloalkyl;    -   n_(D) is 0, 1 or 2;    -   m_(D) is 1 or 2;    -   v_(D) is 0, 1, 2 or 3;        from among these, preference is given to compounds of the type        of the N-acylsulphonamides, for example of the formula (S4^(a))        below, which are known, for example, from WO-A-97/4subchamber16

-   -   in which    -   R_(D) ⁷ is (C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl, where the 2        last-mentioned radicals are substituted by v_(D) substituents        from the group consisting of halogen, (C₁-C₄)-alkoxy,        halo-(C₁-C₆)-alkoxy and (C₁-C₄)-alkylthio and, in the case of        cyclic radicals, also (C₁-C₄)-alkyl and (C₁-C₄)-haloalkyl;    -   R_(D) ⁴ is halogen, (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy, CF₃;    -   m_(D) 1 or 2;    -   v_(D) is 0, 1, 2 or 3;    -   and also    -   acylsulphamoylbenzamides, for example of the formula (S4^(b))        below, which are known, for example, from WO-A-99/16744,

-   -   in which    -   R_(D) ⁵, R_(D) ⁶ independently of one another are hydrogen,        (C₁-C₆)-alkyl, (C₃-C₆)-cycloalkyl, (C₃-C₆)-alkenyl,        (C₃-C₆)-alkynyl,    -   R_(D) ⁴ is halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl or        (C₁-C₄)-alkoxy and    -   m_(D) is 1 or 2,    -   for example those in which    -   R_(D) ⁵=cyclopropyl and (R_(D) ⁴)=2-OMe (“cyprosulphamide”,        S4-1),    -   R_(D) ⁵=cyclopropyl and (R_(D) ⁴)=5-Cl-2-OMe (S4-2),    -   R_(D) ⁵=ethyl and (R_(D) ⁴)=2-OMe (S4-3),    -   R_(D) ⁵=isopropyl and (R_(D) ⁴)=5-C₁₋₂-OMe (S4-4) and    -   R_(D) ⁵=isopropyl and (R_(D) ⁴)=2-OMe (S4-5)        and also    -   compounds of the type of the N-acylsulphamoylphenylureas of the        formula (S4^(c)), which are known, for example, from        EP-A-365484,

-   -   in which    -   R_(D) ⁸ and R_(D) ⁹ independently of one another are hydrogen,        (C₁-C₈)-alkyl, (C₃-C₈)-cycloalkyl, (C₃-C₆)-alkenyl,        (C₃-C₆)-alkynyl,    -   R_(D) ⁴ is halogen, (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy, CF₃,    -   m_(D) is 1 or 2;    -   for example

-   1-[4-(N-2-methoxybenzoylsulphamoyl)phenyl]-3-methylurea,

-   1-[4-(N-2-methoxybenzoylsulphamoyl)phenyl]-3,3-dimethylurea,

-   1-[4-(N-4,5-dimethylbenzoylsulphamoyl)phenyl]-3-methylurea.    -   S5) Active compounds from the class of the hydroxyaromatics and        aromatic-aliphatic carboxylic acid derivatives (S5), for example        ethyl 3,4,5-triacetoxybenzoate, 3,5-dimethoxy-4-hydroxybenzoic        acid, 3,5-dihydroxybenzoic acid, 4-hydroxysalicylic acid,        4-fluorosalicyclic acid, 2-hydroxycinnamic acid,        1,2-dihydro-2-oxo-6-trifluoromethylpyridine-3-carboxamide,        2,4-dichlorocinnamic acid, as described in WO-A-2004/084631,        WO-A-2005/015994, WO-A-2005/016001.    -   S6) Active compounds from the class of the        1,2-dihydroquinoxalin-2-ones (S6), for example        1-methyl-3-(2-thienyl)-1,2-dihydroquinoxalin-2-one,        1-methyl-3-(2-thienyl)-1,2-dihydroquinoxaline-2-thione,        1-(2-aminoethyl)-3-(2-thienyl)-1,2-dihydroquinoxalin-2-one        hydrochloride,        1-[2-(diethylamino)ethyl]-6,7-dimethyl-3-thiophen-2-ylquinoxalin-2(1H)-one,        1-(2-methylsulphonylaminoethyl)-3-(2-thienyl)-1,2-dihydroquinoxalin-2-one,        as described in WO-A-2005/112630.    -   S7) Compounds of the formula (S7), as described in        WO-A-1998/38856,

-   -   where the symbols and indices have the following meanings:    -   R_(E) ¹, R_(E) ² independently of one another are halogen,        (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkyl,        (C₁-C₄)-alkylamino, di-(C₁-C₄)-alkylamino, nitro;    -   A_(E) is COOR_(E) ³ or COSR_(E) ⁴    -   R_(E) ³, R_(E) ⁴ independently of one another are hydrogen,        (C₁-C₄)-alkyl, (C₂-C₆)-alkenyl, (C₂-C₄)-alkynyl, cyanoalkyl,        (C₁-C₄)-haloalkyl, phenyl, nitrophenyl, benzyl, halobenzyl,        pyridinylalkyl or alkylammonium,    -   n_(E) is 0 or 1;    -   n_(E) ², n_(E) ³ independently of one another are 0, 1 or 2,    -   preferably:        -   diphenylmethoxyacetic acid,        -   ethyl diphenylmethoxyacetate,        -   methyl diphenylmethoxyacetate (CAS Reg. No.: 41858-19-9)            (S7-1).    -   S8) Compounds of the formula (S8), as described in        WO-A-98/27049,

-   -   in which    -   X_(F) is CH or N,    -   n_(F) is, if X_(F)=N, an integer from 0 to 4 and        -   is, if X_(F)=CH, an integer from 0 to 5,    -   R_(F) ¹ is halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl,        (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy, nitro, (C₁-C₄)-alkylthio,        (C₁-C₄)-alkylsulphonyl, (C₁-C₄)-alkoxycarbonyl, optionally        substituted phenyl, optionally substituted phenoxy,    -   R_(F) ² is hydrogen or (C₁-C₄)-alkyl,    -   R_(F) ³ is hydrogen, (C₁-C₈)-alkyl, (C₂-C₄)-alkenyl,        (C₂-C₄)-alkynyl or aryl, where each of the carbon-containing        radicals mentioned above is unsubstituted or substituted by one        or more, preferably by up to three, identical or different        radicals from the group consisting of halogen and alkoxy; or        salts thereof,    -   preferably compounds in which    -   X_(F) is CH,    -   n_(F) is an integer from 0 to 2,    -   R_(F) ¹ is halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl,        (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy,    -   R_(F) ² is hydrogen or (C₁-C₄)-alkyl,    -   R_(F) ³ is hydrogen, (C₁-C₈)-alkyl, (C₂-C₄)-alkenyl,        (C₂-C₄)-alkynyl or aryl, where each of the carbon-containing        radicals mentioned above is unsubstituted or substituted by one        or more, preferably by up to three, identical or different        radicals from the group consisting of halogen and alkoxy;        -   or salts thereof,    -   S9) Active compounds from the class of the        3-(5-tetrazolylcarbonyl)-2-quinolones (S9), for example        -   1,2-dihydro-4-hydroxy-1-ethyl-3-(5-tetrazolylcarbonyl)-2-quinolone            (CAS Reg. No.: 219479-18-2),            1,2-dihydro-4-hydroxy-1-methyl-3-(5-tetrazolylcarbonyl)-2-quinolone            (CAS Reg. No.: 95855-00-8), as described in            WO-A-1999/000020.    -   S10) Compounds of the formula (S10^(a)) or (S10^(b))        -   as described in WO-A-2007/023719 and WO-A-2007/023764

-   -   in which    -   R_(G) ¹ is halogen, (C₁-C₄)-alkyl, methoxy, nitro, cyano, CF₃,        OCF₃    -   Y_(G), Z_(G) independently of one another are O or S,    -   n_(G) is an integer from 0 to 4,    -   R_(G) ² is (C₁-C₁₆)-alkyl, (C₂-C₆)-alkenyl, (C₃-C₆)-cycloalkyl,        aryl; benzyl, halobenzyl,    -   R_(G) ³ is hydrogen or (C₁-C₆)-alkyl.    -   S11) Active compounds of the type of the oxyimino compounds        (S11), which are known as seed dressings, such as, for example,        “oxabetrinil”        ((Z)-1,3-dioxolan2-ylmethoxyimino(phenyl)acetonitrile) (S11-1),        which is known as seed dressing safener for millet against        metolachlor damage,        -   “fluxofenim” (1-(4-chlorophenyl)-2,2,2-trifluoro-1-ethanone            O-(1,3-dioxolan-2-ylmethyl)oxime) (S11-2), which is known as            seed dressing safener for millet against metolachlor damage,            and    -   “cyometrinil” or “CGA-43089”        ((Z)-cyanomethoxyimino(phenyl)acetonitrile) (S11-3), which is        known as seed dressing safener for millet against metolachlor        damage.    -   S12) Active compounds from the class of the isothiochromanones        (S12), such as, for example,        methyl[(3-oxo-1H-2-benzothiopyran-4(3H)-ylidene)methoxy]acetate        (CAS Reg. No.: 205121-04-6) (S12-1) and related compounds from        WO-A-1998/13361.    -   S13) One or more compounds from group (S13):        -   “naphthalic anhydride” (1,8-naphthalenedicarboxylic            anhydride) (S13-1), which is known as seed dressing safener            for corn against thiocarbamate herbicide damage,        -   “fenclorim” (4,6-dichloro-2-phenylpyrimidine) (S13-2), which            is known as safener for pretilachlor in sown rice,        -   “flurazole” (benzyl            2-chloro-4-trifluoromethyl-1,3-thiazole-5-carboxylate)            (S13-3), which is known as seed dressing safener for millet            against alachlor and metolachlor damage,        -   “CL-304415” (CAS Reg. No.: 31541-57-8)            (4-carboxy-3,4-dihydro-2H-1-benzopyran-4-acetic acid)            (S13-4) from American Cyanamid, which is known as safener            for corn against imidazolinone damage,        -   “MG-191” (CAS Reg. No.: 96420-72-3)            (2-dichloromethyl-2-methyl-1,3-dioxolane) (S13-5) from            Nitrokemia, which is known as safener for corn,        -   “MG-838” (CAS Reg. No.: 133993-74-5) (2-propenyl            1-oxa-4-azaspiro[4.5]decane-4-carbodithioate) (S13-6) from            Nitrokemia,        -   “disulfoton” (O,O-diethyl S-2-ethylthioethyl            phosphorodithioate) (S13-7),        -   “dietholate” (O,O-diethyl O-phenyl phosphorothioate)            (S13-8),        -   “mephenate” (4-chlorophenyl methylcarbamate) (S13-9).    -   S14) Active compounds which, besides a herbicidal effect against        harmful plants, also have a safener effect on crop plants such        as rice, such as, for example, “dimepiperate” or “MY-93”        (S-1-methyl-1-phenylethyl piperidine-1-carbothioate), which is        known as safener for rice against molinate herbicide damage,        -   “daimuron” or “SK 23”            (1-(1-methyl-1-phenylethyl)-3-p-tolylurea), which is known            as safener for rice against imazosulphuron herbicide damage,        -   “cumyluron”=“JC-940”            (3-(2-chlorophenylmethyl)-1-(1-methyl-1-phenyl-ethyl)urea,            see JP-A-60087254), which is known as safener for rice            against some herbicide damage,        -   “methoxyphenone” or “NK 049”            (3,3′-dimethyl-4-methoxybenzophenone), which is known as            safener for rice against some herbicide damage,        -   “CSB” (1-bromo-4-(chloromethylsulphonyl)benzene) from            Kumiai, (CAS Reg. No. 54091-06-4), which is known as safener            against some herbicide damage in rice.    -   S15) Compounds of the formula (S15) or tautomers thereof

-   -   as described in WO-A-2008/131861 and WO-A-2008/131860    -   in which

-   R_(H) ¹ is a (C₁-C₆)-haloalkyl radical and

-   R_(H) ² is hydrogen or halogen and

-   R_(H) ³, R_(H) ⁴ independently of one another are hydrogen,    (C₁-C₁₆)-alkyl, (C₂-C₁₆)-alkenyl or (C₂-C₁₆)-alkynyl,    -   where each of the 3 last mentioned radicals is unsubstituted or        substituted by one or more radicals from the group consisting of        halogen, hydroxyl, cyano, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy,        (C₁-C₄)-alkylthio, (C₁-C₄)-alkylamino, di[(C₁-C₄)-alkyl]amino,        [(C₁-C₄)-alkoxy]carbonyl, [(C₁-C₄)-haloalkoxy]carbonyl,        unsubstituted or substituted (C₃-C₆)-cycloalkyl, unsubstituted        or substituted phenyl and unsubstituted or substituted        heterocyclyl,    -   or (C₃-C₆)-cycloalkyl, (C₄-C₆)-cycloalkenyl, (C₃-C₆)-cycloalkyl        which is fused at one side of the ring to a 4- to 6-membered        saturated or unsaturated carbocyclic ring, or        (C₄-C₆)-cycloalkenyl which is fused at one side of the ring to a        4- to 6-membered saturated or unsaturated carbocyclic ring,    -   where each of the 4 last mentioned radicals is unsubstituted or        substituted by one or more radicals from the group consisting of        halogen, hydroxyl, cyano, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl,        (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio,        (C₁-C₄)-alkylamino, di[(C₁-C₄)-alkyl]amino,        [(C₁-C₄)-alkoxy]carbonyl, [(C₁-C₄)-haloalkoxy]carbonyl,        unsubstituted or substituted (C₃-C₆)-cycloalkyl, unsubstituted        or substituted phenyl and unsubstituted or substituted        heterocyclyl,    -   or

-   R_(H) ³ is (C₁-C₄)-alkoxy, (C₂-C₄)-alkenyloxy, (C₂-C₆)-alkynyloxy or    (C₂-C₄)-haloalkoxy and

-   R_(H) ⁴ is hydrogen or (C₁-C₄)-alkyl or    -   R_(H) ³ and R_(H) ⁴ together with the directly attached nitrogen        atom are a 4- to 8-membered heterocyclic ring which, in addition        to the nitrogen atom, may also contain further hetero ring        atoms, preferably up to two further hetero ring atoms from the        group consisting of N, O and S, and which is unsubstituted or        substituted by one or more radicals from the group consisting of        halogen, cyano, nitro, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl,        (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy and (C₁-C₄)-alkylthio.    -   S16) Active compounds which are primarily used as herbicides,        but also have safener effect on crop plants, for example

-   (2,4-dichlorophenoxy)acetic acid (2,4-D),

-   (4-chlorophenoxy)acetic acid,

-   (R,S)-2-(4-chloro-o-tolyloxy)propionic acid (mecoprop),

-   4-(2,4-dichlorophenoxy)butyric acid (2,4-DB),

-   (4-chloro-o-tolyloxy)acetic acid (MCPA),

-   4-(4-chloro-o-tolyloxy)butyric acid,

-   4-(4-chlorophenoxy)butyric acid,

-   3,6-dichloro-2-methoxybenzoic acid (dicamba),

-   1-(ethoxycarbonyl)ethyl 3,6-dichloro-2-methoxybenzoate    (lactidichlor-ethyl).

Most preferred crop plant compatibility-improving compounds arecloquintocet-mexyl, fenchlorazole-ethyl, isoxadifen-ethyl,mefenpyr-diethyl, fenclorim, cumyluron, S4-1 and S4-5, and particularemphasis is given to cloquintocet-mexyl and mefenpyr-diethyl.

It has now surprisingly been found that the above-defined activecompound combinations of compounds of the general formula (I) andsafeners (antidotes) from group (b′) set out above combine very goodcompatibility with useful plants with a particularly high herbicidalactivity and can be used in various crops, in particular in cereals(especially wheat), but also in soya beans, potatoes, maize and rice,for the selective control of weeds.

In this context, it is considered surprising that, from a multiplicityof known safeners or antidotes capable of antagonizing the damagingeffect of a herbicidal crop plant, it is specifically the compounds ofgroup (b′) set out above which are suitable for compensating—almostcompletely—the damaging effect of compounds of the formula (I) on thecrop plants, without at the same time having any substantial adverseeffect on the herbicidal activity against the weeds.

Emphasis may be given here to the particularly advantageous effect ofthe preferred and most preferred combination partners from group (b′),particularly with regard to the sparing of cereal plants, such as, forexample, wheat, barley and rye, but also maize and rice, as crop plants.

According to the invention, the preparation of the compounds of theformula (I) can be carried out by processes A to H.

Using, for example, according to process (A)methyl-2-[(2,6-diethyl-4-methylphenyl)acetyl]-4-(1,3-dioxolan-2-yl)cyclopentanecarboxylate, the course of the process according to the invention can berepresented by the reaction scheme below:

Using, for example, according to process (B)2-(2,6-diethyl-4-methylphenyl)-5-(1,3-dioxolan-2-yl)-3-hydroxy-4,5,6,6a-tetrahydropentalen-1(3aH)-oneand pivaloyl chloride as starting materials, the course of the processaccording to the invention can be represented by the reaction schemebelow:

Using, for example, according to process (B)2-(2,6-diethyl-4-methylphenyl)-5-(1,3-dioxolan-2-yl)-3-hydroxy-4,5,6,6a-tetrahydropentalen-1(3aH)-oneand acetic anhydride as starting materials, the course of the processaccording to the invention can be represented by the reaction schemebelow:

Using, for example, according to process (C)2-(2,6-diethyl-4-methylphenyl)-5-(1,3-dioxolan-2-yl)-3-hydroxy-4,5,6,6a-tetrahydropentalen-1(3aH)-oneand ethyl chloroformate as starting materials, the course of the processaccording to the invention can be represented by the reaction schemebelow:

Using, for example, according to process (D)2-(2,6-diethyl-4-methylphenyl)-5-(1,3-dioxolan-2-yl)-3-hydroxy-4,5,6,6a-tetrahydropentalen-1(3aH)-oneand methyl chloromonothioformate as starting materials, the course ofthe process according to the invention can be represented by thereaction scheme below:

Using, for example, according to process (E)5′-(2,6-diethyl-4-methylphenyl)-6′-hydroxy-2,2-dimethyl-1′,3′,3a′,6a′-tetrahydro-4′H-spiro[1,3-dioxolan-4,2′-pentalen]-4′-oneand methanesulphonyl chloride as starting materials, the course of thereaction can be represented by the reaction scheme below:

Using, for example, according to process (F)2-(2,6-diethyl-4-methylphenyl)-5-(1,3-dioxolan-2-yl)-3-hydroxy-4,5,6,6a-tetrahydropentalen-1(3aH)-one and 2,2,2-trifluoroethylmethanethiophosphonyl chloride asstarting materials, the course of the reaction can be represented by thereaction scheme below:

Using, for example, according to process (G)2-(2,6-diethyl-4-methylphenyl)-5-(1,3-dioxolan-2-yl)-3-hydroxy-4,5,6,6a-tetrahydropentalen-1(3aH)-oneand NaOH as components, the course of the process according to theinvention can be represented by the reaction scheme below:

Using, for example, according to process (H), variant a,2-(2,6-diethyl-4-methylphenyl)-5-(1,3-dioxolan-2-yl)-3-hydroxy-4,5,6,6a-tetrahydropentalen-1(3aH)-oneand ethyl isocyanate as starting materials, the course of the reactioncan be represented by the reaction scheme below:

Using, for example, according to process (H), variant B,2-(2,6-diethyl-4-methylphenyl)-5-(1,3-dioxolan-2-yl)-3-hydroxy-4,5,6,6a-tetrahydropentalen-1(3aH)-one and dimethylcarbamoyl chloride as starting materials, thecourse of the reaction may be represented by the scheme below:

The compounds, required as starting material in process (A) according tothe invention, of the formula (II)

in which

-   Q, Y, R¹, R², R³, R⁴ and R⁵ have the meaning given above, and-   R²⁶ represents alkyl (in particular C₁-C₈-alkyl)    are novel. They can be prepared by methods known in principle by    esterifying 5-aryl-4-ketocarboxylic acids of the formula (XIII)

in which

-   Q, Y, R¹, R², R³, R⁴ and R⁵ have the meaning given above    in a conventional manner (cf., for example, Organikum, 15th Edition,    Berlin, 1977, page 499 or Preparation Example).

Compounds of the formula (XIII) are likewise novel, they can be preparedby methods known in principle (WO 07/080,066, WO 96/01 798, WO 97/14667,WO 98/39281, WO 01/74770), for example, by decarboxylating2-phenyl-3-oxoadipic esters of the formula (XIV)

-   in which Q, Y, R¹, R², R³, R⁴ and R⁵R²⁶ have the meaning given above    and-   R²⁶ represents alkyl (in particular C₁-C₈-alkyl) or, if the    preparation uses the anhydrides of the formula (XVI), represents    hydrogen,-   R³³ represents alkyl (in particular C₁-C₈-alkyl),    if appropriate in the presence of a diluent and if appropriate in    the presence of a base or acid according to conventional methods    (cf., for example, Organikum, 15th Edition, Berlin, 1977, pages    519-521).

The compounds of the formula (XIV) are likewise novel in principle andcan be prepared in accordance with known methods. The compounds of theformula (XIV) are obtained, for example, by reacting dicarboxylicsemiester chlorides of the formula (XV)

in which

-   Q, Y, R and R⁵ have the meaning given above and-   Hal represents chlorine or bromine    or carboxylic anhydrides of the formula (XVI)

in which

-   Q, Y and R⁵ have the meaning given above    with a phenylacetic ester of the formula (XVII)

in which

-   R, R¹, R², R³, R⁴, R⁵ and R³³ have the meaning given above    in the presence of a diluent and in the presence of a base (cf., for    example, M. S. Chambers, E. J. Thomas, D. J. Williams, J. Chem. Soc.    Chem. Commun, (1987), 1228).

A further proven method for preparing the compounds, required asstarting materials for process (A), of the formula (II)

in which

-   Q, Y, R¹, R², R³, R⁴ and R⁵ have the meaning given above    is also, for example, the coupling of benzyl zinc compounds of the    formula (XVIII)

in which R¹, R², R³ and R⁴ have the meaning given above and Halrepresents a halogen atom, preferably chlorine or bromine,if appropriate in the presence of a catalyst, with a dicarboxylicsemiester chloride of the formula (XV) or a carboxylic anhydride of theformula (XVI).

Both the preparation and the reaction of organic zinc compounds withcarbonyl chlorides and carboxylic anhydrides are known in principle andcan be carried out in close analogy to the processes described in theliterature. More details are described, for example, in Chem. Commun2008, 5824, WO 2007/113294, WO 2010/040460, Tetrahedron Letters 30,5069-5072 (1989) or Chem. Rev. 1993, 93, 2117-2188.

The acid halides of the formula (III), carboxylic anhydrides of theformula (IV), chloroformic esters or chloroformic thioesters of theformula (V), chloromonothioformic esters or chlorodithioformic esters ofthe formula (VI), sulphonyl chlorides of the formula (VII), phosphoruscompounds of the formula (VIII) and metal hydroxides, metal alkoxides oramines of the formulae (IX) and (X) and isocyanates of the formula (XI)and carbamoyl chlorides of the formula (XII) furthermore required asstarting materials for carrying out the processes (B), (C), (D), (E),(F), (G) and (H) according to the invention are generally knowncompounds of organic of inorganic chemistry.

The compounds of the formulae (XV), (XVI), (XVII) and (XVIII) are knowncompounds of organic chemistry or known from the patent applicationscited at the outset and/or can be prepared in a simple manner by methodsknown in principle or can be prepared by the methods described in thepatent applications cited at the outset.

The process (A) is characterized in that compounds of the formula (II),in which Q, Y, R¹, R², R³, R⁴ and R⁵ have the meaning given above aresubjected to an intramolecular condensation in the presence of a base.

Suitable for use as diluents in the process (A) according to theinvention are all organic solvents which are inert towards the reactionparticipants. Preference is given to using hydrocarbons, such as tolueneand xylene, furthermore ethers, such as bibutyl ether, tetrahydrofuran,dioxane, glycol dimethyl ether and diglycol dimethyl ether, moreoverpolar solvents, such as dimethyl sulphoxide, sulpholane,dimethylformamide and N-methylpyrrolidone. It is furthermore possible touse alcohols, such as methanol, ethanol, propanol, isopropanol, butanol,isobutanol, tert-butanol.

Suitable bases (deprotonating agents) for carrying out the process (A)according to the invention are all customary proton acceptors.Preference is given to using alkali metal and alkaline earth metaloxides, hydroxides and carbonates, such as sodium hydroxide, potassiumhydroxide, magnesium oxide, calcium oxide, sodium carbonate, potassiumcarbonate and calcium carbonate, which may also be used in the presenceof phase-transfer catalysts, such as, for example,triethylbenzylammonium chloride molar amounts. However, it is alsopossible to use a relatively large excess (up to 3 mol) of one componentor the other.

The process (B-α) is characterized in that compounds of the formula(I-a) are in each case reacted with carbonyl halides of the formula(III), if appropriate in the presence of a diluent and if appropriate inthe presence of an acid binder.

Suitable for use as diluents in the process (B-α) according to theinvention are all solvents which are inert towards the acid halides.Preference is given to using hydrocarbons, such as benzine, benzene,toluene, xylene and tetralin, furthermore halogenated hydrocarbons, suchas methylene chloride, chloroform, carbon tetrachloride, chlorobenzeneand o-dichlorbenzene, moreover ketones, such as acetone and methylisopropyl ketone, furthermore ethers, such as diethyl ether,tetrahydrofuran and dioxane, additionally carboxylic esters, such asethyl acetate, and also strongly polar solvents, such as dimethylsulphoxide and sulpholan. If the acid halide is sufficiently stable tohydrolysis, the reaction can also be carried out in the presence ofwater.

Suitable acid binders for the reaction according to process (B-α)according to the invention are all customary acid acceptors. Preferenceis given to using tertiary amines, such as triethylamine, pyridine,diazabicyclooctane (DABCO), diazabicycloundecene (DBU),diazabicyclononene (DBN), Hünig-Base and N,N-dimethylaniline,furthermore alkaline earth metal oxides, such as magnesium oxide andcalcium oxide, moreover alkali metal carbonates and alkaline earth metalcarbonates, such as sodium carbonate, potassium carbonate and calciumcarbonate, and also alkali metal hydroxides, such as sodium hydroxideand potassium hydroxide.

The reaction temperatures in the process (B-α) according to theinvention can be varied within a relatively wide range. In general, theprocess is carried out at temperatures between −20° C. and +150° C.,preferably between 0° C. and 100° C.

When carrying out the process (B-α) according to the invention, thestarting materials of the formula (I-a) and the carbonyl halide of theformula (III) are generally each employed in approximately equivalentamounts. However, it is also possible to use a relatively large excess(up to 5 mol) of the carbonyl halide. Work-up is carried out bycustomary methods.

The process (B-β) is characterized in that compounds of the formula(I-a) are reacted with carboxylic anhydrides of the formula (IV), ifappropriate in the presence of a diluent and if appropriate in thepresence of an acid binder.

Suitable diluents for use in the process (B-β) according to theinvention are, preferably, the diluents which are also preferred whenusing acid halides. Besides this a carboxylic anhydride used in excessmay simultaneously act as diluent.

Suitable acid binders, which are added, if appropriate, for process(B-β) are, preferably, the acid binders which are also preferred whenusing acid halides.

The reaction temperatures in the process (B-β) according to theinvention may be varied within a relatively wide range. In general, theprocess is carried out at temperatures between −20° C. and +150° C.,preferably between 0° C. and 100° C.

When carrying out the process (B-β) according to the invention, thestarting materials of the formula (I-a) and the carboxylic anhydride ofthe formula (IV) are generally each employed in approximately equivalentamounts. However, it is also possible to use a relatively large excess(up to 5 mol) of carboxylic anhydride. Work-up is carried out bycustomary methods.

In general, diluent and excess carboxylic anhydride and the carboxylicacid formed are removed by distillation or by washing with an organicsolvent or with water.

The process (C) is characterized in that compounds of the formula (I-a)are in each case reacted with chloroformic esters or chloroformic thioesters of the formula (V), if appropriate in the presence of a diluentand if appropriate in the presence of an acid binder.

Suitable acid binders for the reaction according to the process (C)according to the invention are all customary acid acceptors. Preferenceis given to use tertiary amines, such as triethylamine, pyrridine,DABCO, DBU, DBA, Hünig-Base and N,N-dimethylaniline, furthermorealkaline earth metal oxides, such as magnesium oxide and calcium oxide,moreover alkali metal carbonates and alkaline earth metal carbonates,such as sodium carbonate, potassium carbonate and calcium carbonate, andalso alkali metal hydroxides, such as sodium hydroxide and potassiumhydroxide.

Suitable diluents for use in the process (C) according to the inventionare all solvents which are inert towards the chloroformic esters orchloroformic thio esters. Preference is given to using hydrocarbons,such as benzine, benzene, toluene, xylene and tetralin, furthermorehalogenated hydrocarbons, such as methylene chloride, chloroform, carbontetrachloride, chlorobenzene and o-dichlorobenzene, moreover ketones,such as acetone and methyl isopropyl ketone, furthermore ethers, such asdiethyl ether, tetrahydrofuran and dioxane, additionally carboxylicesters, such as ethyl acetate, and also strongly polar solvents, such asdimethyl sulphoxide and sulpholan.

When carrying out the process (C) according to the invention, thereaction temperatures can be varied within a relatively wide range. Ifthe process is carried out in the presence of a diluent and an acidbinder, the reaction temperatures are generally between −20° C. and+100° C., preferably between 0° C. and 50° C.

The process (C) according to the invention is generally carried outunder atmospheric pressure.

When carrying out the process (C) according to the invention, thestarting materials of the formula (I-a) and the appropriate chloroformicester or chloroformic thio ester of the formula (V) are generally eachemployed in approximately equivalent amounts. However, it is alsopossible to use a relatively large excess (up to 2 mol) of one componentor the other. Work-up is carried out by customary methods. In general,precipitated salts are removed and the reaction mixture that remains isconcentrated by removing the diluent under reduced pressure.

The process (D) according to the invention is characterized in thatcompounds of the formula (I-a) are in each case reacted with compoundsof the formula (VI) in the presence of a diluent and, if appropriate, inthe presence of an acid binder.

In preparation process (D), about one mol of chloromonothioformic esteror chlorodithioformic ester of the formula (VI) is employed per mole ofthe starting material of the formula (I-a) at from 0 to 120° C.,preferably from 20 to 60° C.

Suitable diluents which are added, if appropriate, are all inert polarorganic solvents, such as ethers, amides, sulphones, sulphoxides, andalso halogenated alkanes.

Preference is given to using dimethyl sulphoxide, tetrahydrofuran,dimethylformamide or methylene chloride.

If, in a preferred embodiment, the enolate salt of the compounds (1-a)is prepared by addition of strong deprotonating agents, such as, forexample, sodium hydride or potassium tert-butoxide, the further additionof acid binders may be dispensed with.

If acid binders are used, these are customary inorganic or organicbases; sodium hydroxide, sodium carbonate, potassium carbonate, pyridineand triethylamine may be mentioned by way of example.

The reaction can be carried out at atmospheric pressure or underelevated pressure and is preferably carried out at atmospheric pressure.Work-up is carried out by customary methods.

The process (E) according to the invention is characterized in thatcompounds of the formula (I-a) are in each case reacted with sulphonylchlorides of the formula (VII), if appropriate in the presence of adiluent and if appropriate in the presence of an acid binder.

In preparation process (E), about one mol of sulphonyl chloride of theformula (VII) is reacted per mole of the starting material of theformula (I-a) at from −20 to 150° C., preferably from 20 to 70° C.

Suitable diluents which are added, if appropriate, are all inert polarorganic solvents, such as ethers, amides, nitrides, sulphones,sulphoxides or halogenated hydrocarbons, such as methylene chloride.

Preference is given to using dimethyl sulphoxide, tetrahydrofuran,dimethylformamide, methylene chloride.

If, in a preferred embodiment, the enolate salt of the compounds (1-a)is prepared by addition of strong deprotonating agents (such as, forexample, sodium hydride or potassium tert-butoxide), the furtheraddition of acid binders may be dispensed with.

If acid binders are used, these are customary inorganic or organicbases, for example sodium hydroxide, sodium carbonate, potassiumcarbonate, pyridine and triethylamine.

The reaction can be carried out at atmospheric pressure or underelevated pressure and is preferably carried out at atmospheric pressure.Work-up is carried out by customary methods.

The process (F) according to the invention is characterized in thatcompounds of the formula (I-a) are in each case reacted with phosphoruscompounds of the formula (VIII), if appropriate in the presence of adiluent and if appropriate in the presence of an acid binder.

In preparation process (F), to obtain compounds of the formula (I-e),from 1 to 2, preferably from 1 to 1.3, mol of the phosphorus compound ofthe formula (VIII) are reacted per mole of the compounds of the formula(I-a), at temperatures between −40° C. and 150° C., preferably between−10 and 110° C.

Suitable diluents which are added, if appropriate, are all inert polarorganic solvents, such as ethers, amides, nitriles, alcohols, sulphides,sulphones, sulphoxides, etc.

Preference is given to using acetonitrile, dimethyl sulphoxide,tetrahydrofuran, dimethylformamide, methylene chloride.

Suitable acid binders which are added, if appropriate, are customaryinorganic or organic bases, such as hydroxides, carbonates or amines.Sodium hydroxide, sodium carbonate, potassium carbonate, pyridine andtriethylamine may be mentioned by way of example.

The reaction can be carried out at atmospheric pressure or underelevated pressure and is preferably carried out at atmospheric pressure.Work-up is carried out by customary methods of organic chemistry. Thearising end products are preferably purified by crystallization,chromatographic purification or “incipient distillation” i.e. removal ofthe volatile components under reduced pressure.

The process (G) is characterized in that compounds of the formula (I-a)are reacted with metal hydroxides or metal alkoxides of the formula (IX)or amines of the formula (X), if appropriate in the presence of adiluent.

Suitable diluents for use in the process (G) according to the inventionare, preferably, ethers, such as tetrahydrofuran, dioxane, diethylether, or else alcohols, such as methanol, ethanol, isopropanol, andalso water.

The process (G) according to the invention is generally carried outunder atmospheric pressure.

The reaction temperatures are generally between −20° C. and 100° C.,preferably between 0° C. and 50° C.

The process (H) according to the invention is characterized in thatcompounds of the formula (I-a) are in each case reacted with (H-α)compounds of the formula (XI), if appropriate in the presence of adiluent and if appropriate in the presence of a catalyst, or (H-β) withcompounds of the formula (XII), if appropriate in the presence of adiluent and if appropriate in the presence of an acid binder.

In preparation process (H-α), about 1 mol of isocyanate of the formula(XI) is reacted per mole of starting material of the formula (I-a), atfrom 0 to 100° C., preferably from 20 to 50° C.

Suitable diluents which are added, if appropriate, are all inert organicsolvents, such as ethers, amides, nitrides, sulphones, sulphoxides.

If appropriate, catalysts may be added to accelerate the reaction.Suitable for use as catalysts are, very advantageously, organotincompounds, such as, for example dibutyl tin dilaurate. The reaction ispreferably carried out at atmospheric pressure.

In preparation process (H-β), about 1 mol of carbamoyl chloride of theformula (XII) is reacted per mole of starting material of the formula(I-a), at from −20 to 150° C., preferably at from 0 to 70° C.

Suitable diluents which are added, if appropriate, are all inert polarorganic solvents, such as ethers, amides, sulphones, sulphoxides orhalogenated hydrocarbons.

Preference is given to using dimethyl sulphoxide, tetrahydrofuran,dimethylformamide or methylene chloride.

If, in a preferred embodiment, the enolate salt of the compound of theformula (I-a) is prepared by addition of strong deprotonating agents(such as, for example, sodium hydride or potassium tert-butoxide), thefurther addition of acid binders may be dispensed with.

If acid binders are used, then customary inorganic or organic bases aresuitable, for example sodium hydroxide, sodium carbonate, potassiumcarbonate, triethylamine or pyridine.

The reaction can be carried at an atmospheric pressure or under elevatedpressure and is preferably carried out at atmospheric pressure. Work-upis carried out by customary methods.

In the literature it has already been described how the action ofvarious active compounds can be boosted by addition of ammonium salts.The salts in question, however, are detersive salts (for example WO95/017817) or salts which have relatively long alkyl substituents and/oraryl substituents and which have a permeabilizing action or whichincrease the active compound's solubility (for example EP-A 0 453 086,EP-A 0 664 081, FR-A 2 600 494, U.S. Pat. No. 4,844,734, U.S. Pat. No.5,462,912, U.S. Pat. No. 5,538,937, US-A 03/0224939, US-A 05/0009880,US-A 05/0096386). Moreover, the prior art describes the action only forparticular active compounds and/or particular applications of thecorresponding compositions. In other cases, in turn, the salts inquestion are those of sulphonic acids, where the acids themselves have aparalytic action on insects (U.S. Pat. No. 2,842,476). A boost to actionby ammonium sulphate, for example, is described by way of example forthe herbicides glyphosate, phosphinothricin and for phenyl-substitutedcyclic ketoenols (U.S. Pat. No. 6,645,914, EP-A2 0 036 106, WO07/068,427). A corresponding boost of action in the case of insecticideshas already been described in WO 07/068,428.

The use of ammonium sulphate as a formulating assistant has also beendescribed for certain active compounds and applications (WO 92/16108),but its purpose therein is to stabilize the formulation, not to boostthe action.

It has now been found, surprisingly, that the action of insecticidesand/or acaricides and/or herbicides from the class of thephenyl-substituted bicyclooctane-1,3-dione derivatives of the formula(I) can be boosted significantly through the addition of ammonium saltsor phosphonium salts to the application solution or through theincorporation of these salts into a formulation comprisingphenyl-substituted bicyclooctane-1,3-dione derivatives of the formula(I). The present invention therefore provides for the use of ammoniumsalts or phosphonium salts for boosting the action of crop protectioncompositions which comprise as their active compound herbicidal and/orinsecticidal and/or acaricidal phenyl-substitutedbicyclooctane-1,3-dione derivatives of the formula (I). The inventionlikewise provides compositions which comprise herbicidal and/oracaricidal and/or insecticidal phenyl-substitutedbicyclooctane-1,3-dione derivatives of the formula (I) andaction-boosting ammonium salts or phosphonium salts, including not onlyformulated active compounds but also ready-to-use compositions (sprayliquors). The invention further provides, finally, for the use of thesecompositions for controlling insect pests and/or spider mites and/orunwanted vegetation.

The active compounds can be used in the compositions according to theinvention in a broad concentration range. The concentration of theactive compounds in the formulation is typically 0.1%-50% by weight.

Formula (III′) provides a definition of the ammonium salts andphosphonium salts which, according to the invention, boost the activityof crop protection compositions comprising fatty acid biosynthesisinhibitors

in whichD represents nitrogen or phosphorus,D preferably represents nitrogen,R^(26′), R^(27′), R^(28′) and R^(29′) independently of one anotherrepresent hydrogen or in each case optionally substituted C₁-C₈-alkyl ormono- or polyunsaturated, optionally substituted C₁-C₈-alkylene, thesubstituents being selectable from halogen, nitro and cyano,R^(26′), R^(27′), R^(28′) and R^(29′) independently of one anotherpreferably represent hydrogen or in each case optionally substitutedC₁-C₄-alkyl, the substituents being selectable from halogen, nitro andcyano,R^(26′), R^(27′), R^(28′) and R^(29′) independently of one anotherparticularly preferably represent hydrogen, methyl, ethyl, n-propyl,isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl,R^(26′), R^(27′), R^(28′) and R^(29′) very particularly preferablyrepresent hydrogen,n represents 1, 2, 3 or 4,n preferably represents 1 or 2,R^(30′) represents an organic or inorganic anion,R^(30′) preferably represents hydrogencarbonate, tetraborate, fluoride,bromide, iodide, chloride, monohydrogenphosphate, dihydrogenphosphate,hydrogensulphate, tartrate, sulphate, nitrate, thiosulphate,thiocyanate, formate, lactate, acetate, propionate, butyrate, pentanoateor oxalate,R^(30′) particularly preferably represents lactate, sulphate, nitrate,thiosulphate, thiocyanate, oxalate or formate.R^(30′) very particularly preferably represents sulphate.

The ammonium salts and phosphonium salts of the formula (III′) can beused in a broad concentration range to boost the activity of cropprotection compositions comprising phenyl-substitutedbicyclooctane-1,3-dione derivatives of the formula (I). In general theammonium salts or phosphonium salts are used in the ready-to-use cropprotection composition in a concentration of 0.5 to 80 mmol/l,preferably 0.75 to 37.5 mmol/l, more preferably 1.5 to 25 mmol/l. In thecase of a formulated product the ammonium salt and/or phosphonium saltconcentration in the formulation is chosen such that it is within thesestated general, preferred or particularly preferred ranges after theformulation has been diluted to the desired active compoundconcentration. The concentration of the salt in the formulation istypically 1%-50% by weight.

In one preferred embodiment of the invention the activity is boosted byadding to the crop protection compositions not only an ammonium saltand/or phosphonium salt but also, additionally, a penetrant. It isconsidered entirely surprising that even in these cases an even greaterboost to activity is observed. The present invention therefore likewiseprovides for the use of a combination of penetrant and ammonium saltsand/or phosphonium salts to boost the activity of crop protectioncompositions which comprise insecticidal and/or acaricidal and/orherbicidal phenyl-substituted bicyclooctane-1,3-dione derivatives of theformula (I) as active compound. The invention likewise providescompositions which comprise herbicidal and/or acaricidal and/orinsecticidal phenyl-substituted bicyclooctane-1,3-dione derivatives ofthe formula (I), penetrants and ammonium salts and/or phosphonium salts,including specifically not only formulated active compounds but alsoready-to-use compositions (spray liquors). The invention additionallyprovides, finally, for the use of these compositions for controllingharmful insects and/or spider mites and/or unwanted vegetation.

In the present context, suitable penetrants are all those substanceswhich are usually employed to improve penetration of agrochemicallyactive compounds into plants. In this context, penetrants are defined inthat they penetrate from the aqueous spray liquor and/or the spraycoating into the cuticles of the plant, thus increasing the mobility ofactive compounds in the cuticles. The method described in the literature(Baur et al., 1997, Pesticide Science 51, 131-152) can be used fordetermining this property.

Examples of suitable penetrants include alkanol alkoxylates. Penetrantsof the invention are alkanol alkoxylates of the formula (IV′)R—O-(−AO)_(v)—R′  (IV′)in which

-   R represents straight-chain or branched alkyl having 4 to 20 carbon    atoms,-   R′ represents hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl,    isobutyl, tert-butyl, n-pentyl or n-hexyl,-   AO represents an ethylene oxide radical, a propylene oxide radical,    a butylene oxide radical or represents mixtures of ethylene oxide    and propylene oxide radicals or butylene oxide radicals, and-   v represents a number from 2 to 30.    One preferred group of penetrants are alkanol alkoxylates of the    formula    R—O-(−EO—)_(n)—R′  (IV′-a)    in which-   R is as defined above,-   R′ is as defined above,-   EO represents —CH₂—CH₂—O—, and-   n represents a number from 2 to 20.

A further preferred group of penetrants are alkanol alkoxylates of theformulaR—O-(−EO—)_(p)—(—PO—)_(q)—R′  (IV′-b)in which

-   R is as defined above,-   R′ is as defined above,-   EO represents —CH₂—CH₂—O—,-   PO represents

-   represents a number from 1 to 10, and-   q represents a number from 1 to 10.

A further preferred group of penetrants are alkanol alkoxylates of theformulaR—O—(—PO—)_(r)-(EO—)_(s)—R′  (IV′-c)in which

-   R is as defined above,-   R′ is as defined above,-   EO represents —CH₂—CH₂—O—,-   PO represents

-   r is a number from 1 to 10, and-   s is a number from 1 to 10.

A further preferred group of penetrants are alkanol alkoxylates of theformulaR—O-(−EO—)_(p)—(—BO—)_(q)—R′  (IV′-d)in which

-   R and R are as defined above,-   EO represents —CH₂—CH₂—O—,-   BO represents

-   is a number from 1 to 10 and-   q is a number from 1 to 10.

A further preferred group of penetrants are alkanol alkoxylates of theformulaR—O—(—BO-)_(r)-(−EO—)_(s)—R′  (IV′-e)in which

-   R and R′ are as defined above,-   BO represents

-   EO represents —CH₂—CH₂—O—,-   r represents a number from 1 to 10 and-   s represents a number from 1 to 10.

A further preferred group of penetrants are alkanol alkoxylates of theformulaCH₃—(CH₂)_(t)—CH₂—O—(—CH₂—CH₂—O—)_(u)R′  (IV′-f)in which

-   R′ is as defined above,-   t represents a number from 8 to 13,-   u represents a number from 6 to 17.

In the formulae indicated above,

-   R preferably represents butyl, isobutyl, n-pentyl, isopentyl,    neopentyl, n-hexyl, isohexyl, n-octyl, isooctyl, 2-ethylhexyl,    nonyl, isononyl, decyl, n-dodecyl, isododecyl, lauryl, myristyl,    isotridecyl, trimethylnonyl, palmityl, stearyl or eicosyl.

As an example of an alkanol alkoxylate of the formula (IV′-c) mentionmay be made of 2-ethylhexyl alkoxylate of the formula

in which

-   EO represents —CH₂—CH₂—O—,-   PO represents

andthe numbers 8 and 6 represent average values.

As an example of an alkanol alkoxylate of the formula (IV′-d) mentionmay be made of the formulaCH₃—(CH₂)₁₀—O-(−EO—)₆—(−BO—)₂—CH₃  (IV′-d-1)in which

-   EO represents —CH₂—CH₂—O—,-   BO represents

andthe numbers 10, 6 and 2 represent average values.

Particularly preferred alkanol alkoxylates of the formula (IV′-f) arecompounds of this formula in which

-   t represents a number from 9 to 12 and-   u represents a number from 7 to 9.

Mention may be made with very particular preference of alkanolalkoxylate of the formula (IV′-f-1)CH₃—(CH₂)_(t)—CH₂—O—(—CH₂—CH₂—O—)_(u)H  (IV′-f-1)in which

-   t represents the average value 10.5 and-   u represents the average value 8.4.

A general definition of the alkanol alkoxylates is given by the formulaeabove. These substances are mixtures of compounds of the stated typewith different chain lengths. The indices therefore have average valueswhich may also deviate from whole numbers.

The alkanol alkoxylates of the formulae stated are known and in somecases are available commercially or can be prepared by known methods(cf. WO 98/35 553, WO 00/35 278 and EP-A 0 681 865).

Suitable penetrants also include, for example, substances which promotethe availability of the compounds of the formula (I) in the spraycoating. These include, for example, mineral or vegetable oils. Suitableoils are all mineral or vegetable oils—modified or otherwise—which cantypically be used in agrochemical compositions. Mention may be made byway of example of sunflower oil, rapeseed oil, olive oil, castor oil,colza oil, maize seed oil, cotton seed oil and soya bean oil, or theesters of said oils. Preference is given to rapeseed oil, sunflower oiland their methyl or ethyl esters.

The concentration of penetrant in the compositions of the invention canbe varied within a wide range. In the case of a formulated cropprotection composition it is in general 1% to 95%, preferably 1% to 55%,more preferably 15%-40% by weight. In the ready-to-use compositions(spray liquors) the concentrations are generally between 0.1 and 10 g/l,preferably between 0.5 and 5 g/l.

Crop protection compositions of the invention may also comprise furthercomponents, examples being surfactants and/or dispersing assistants oremulsifiers.

Suitable nonionic surfactants and/or dispersing assistants include allsubstances of this type that can typically be used in agrochemicalcompositions. Preferably mention may be made of polyethyleneoxide-polypropylene oxide block copolymers, polyethylene glycol ethersof linear alcohols, reaction products of fatty acids with ethylene oxideand/or propylene oxide, and also polyvinyl alcohol,polyvinylpyrrolidone, copolymers of polyvinyl alcohol andpolyvinylpyrrolidone, and copolymers of (meth)acrylic acid and(meth)acrylic esters, and additionally alkyl ethoxylates and alkylarylethoxylates, which optionally may be phosphated and optionally may beneutralized with bases, mention being made, by way of example, ofsorbitol ethoxylates, and, as well, polyoxyalkylenamine derivatives.

Suitable anionic surfactants include all substances of this type thatcan typically be used in agrochemical compositions. Preference is givento alkali metal salts and alkaline earth metal salts of alkylsulphonicacids or alkylarylsulphonic acids.

A further preferred group of anionic surfactants and/or dispersingassistants are the following salts that are of low solubility in plantoil: salts of polystyrenesulphonic acids, salts of polyvinylsulphonicacids, salts of naphthalenesulphonic acid-formaldehyde condensationproducts, salts of condensation products of naphthalenesulphonic acid,phenolsulphonic acid and formaldehyde, and salts of lignosulphonic acid.

Suitable additives which may be included in the formulations of theinvention are emulsifiers, foam inhibitors, preservatives, antioxidants,colorants and inert filling materials.

Preferred emulsifiers are ethoxylated nonylphenols, reaction products ofalkylphenols with ethylene oxide and/or propylene oxide, ethoxylatedarylalkylphenols, and also ethoxylated and propoxylatedarylalkylphenols, and also sulphated or phosphated arylalkyl ethoxylatesand/or arylalkyl ethoxypropoxylates, mention being made by way ofexample of sorbitan derivatives, such as polyethylene oxide-sorbitanfatty acid esters, and sorbitan fatty acid esters.

The active compounds of the invention, in combination with good planttolerance and favourable toxicity to warm-blooded animals and beingtolerated well by the environment, are suitable for protecting plantsand plant organs, for increasing the harvest yields, for improving thequality of the harvested material and for controlling animal pests, inparticular insects, arachnids, helminths, nematodes and molluscs, whichare encountered in agriculture, in horticulture, in animal husbandry, inforests, in gardens and leisure facilities, in the protection of storedproducts and of materials, and in the hygiene sector. They may bepreferably employed as crop protection agents. They are active againstnormally sensitive and resistant species and against all or some stagesof development. The abovementioned pests include:

From the order of the Anoplura (Phthiraptera), for example, Damaliniaspp., Haematopinus spp., Linognathus spp., Pediculus spp., Trichodectesspp.

From the class of the Arachnida, for example, Acarus spp., Aceriasheldoni, Aculops spp., Aculus spp., Amblyomma spp., Amphitetranychusviennensis, Argas spp., Boophilus spp., Brevipalpus spp., Bryobiapraetiosa, Chorioptes spp., Dermanyssus gallinae, Eotetranychus spp.,Epitrimerus pyri, Eutetranychus spp., Eriophyes spp., Halotydeusdestructor, Hemitarsonemus spp., Hyalomma spp., Ixodes spp., Latrodectusmactans, Metatetranychus spp., Nuphersa spp., Oligonychus spp.,Ornithodoros spp., Panonychus spp., Phyllocoptruta oleivora,Polyphagotarsonemus latus, Psoroptes spp., Rhipicephalus spp.,Rhizoglyphus spp., Sarcoptes spp., Scorpio maurus, Stenotarsonemus spp.,Tarsonemus spp., Tetranychus spp., Vasates lycopersici.

From the class of the Bivalva, for example, Dreissena spp.

From the order of the Chilopoda, for example, Geophilus spp., Scutigeraspp.

From the order of the Coleoptera, for example, Acalymma vittatum,Acanthoscelides obtectus, Adoretus spp., Agelastica alni, Agriotes spp.,Amphimallon solstitialis, Anobium punctatum, Anoplophora spp.,Anthonomus spp., Anthrenus spp., Apion spp., Apogonia spp., Atomariaspp., Attagenus spp., Bruchidius obtectus, Bruchus spp., Cassida spp.,Cerotoma trifurcata, Ceutorrhynchus spp., Chaetocnema spp., Cleonusmendicus, Conoderus spp., Cosmopolites spp., Costelytra zealandica,Ctenicera spp., Curculio spp., Cryptorhynchus lapathi, Cylindrocopturusspp., Dermestes spp., Diabrotica spp., Dichocrocis spp., Diloboderusspp., Epilachna spp., Epitrix spp., Faustinus spp., Gibbium psylloides,Hellula undalis, Heteronychus arator, Heteronyx spp., Hylamorphaelegans, Hylotrupes bajulus, Hypera postica, Hypothenemus spp.,Lachnosterna consanguinea, Lema spp., Leptinotarsa decemlineata,Leucoptera spp., Lissorhoptrus oryzophilus, Lixus spp., Luperodes spp.,Lyctus spp., Megascelis spp., Melanotus spp., Meligethes aeneus,Melolontha spp., Migdolus spp., Monochamus spp., Naupactusxanthographus, Niptus hololeucus, Oryctes rhinoceros, Oryzaephilussurinamensis, Oryzaphagus oryzae, Otiorrhynchus spp., Oxycetoniajucunda, Phaedon cochleariae, Phyllophaga spp., Phyllotreta spp.,Popillia japonica, Premnotrypes spp., Psylliodes spp., Ptinus spp.,Rhizobius ventralis, Rhizopertha dominica, Sitophilus spp., Sphenophorusspp., Sternechus spp., Symphyletes spp., Tanymecus spp., Tenebriomolitor, Tribolium spp., Trogoderma spp., Tychius spp., Xylotrechusspp., Zabrus spp.

From the order of the Collembola, for example, Onychiurus armatus.

From the order of the Diplopoda, for example, Blaniulus guttulatus.

From the order of the Diptera, for example, Aedes spp., Agromyza spp.,Anastrepha spp., Anopheles spp., Asphondylia spp., Bactrocera spp.,Bibio hortulanus, Calliphora erythrocephala, Ceratitis capitata,Chironomus spp., Chrysomyia spp., Cochliomyia spp., Contarinia spp.,Cordylobia anthropophaga, Culex spp., Cuterebra spp., Dacus oleae,Dasyneura spp., Delia spp., Dermatobia hominis, Drosophila spp.,Echinocnemus spp., Fannia spp., Gastrophilus spp., Hydrellia spp.,Hylemyia spp., Hyppobosca spp., Hypoderma spp., Liriomyza spp., Luciliaspp., Musca spp., Nezara spp., Oestrus spp., Oscinella frit, Pegomyiaspp., Phorbia spp., Prodiplosis spp., Psila rosae, Rhagoletis spp.,Stomoxys spp., Tabanus spp., Tannia spp., Tetanops spp., Tipula spp.

From the class of the Gastropoda, for example, Arion spp., Biomphalariaspp., Bulinus spp., Deroceras spp., Galba spp., Lymnaea spp.,Oncomelania spp., Pomacea spp., Succinea spp.

From the class of the helminths, for example, Ancylostoma duodenale,Ancylostoma ceylanicum, Acylostoma braziliensis, Ancylostoma spp.,Ascaris lubricoides, Ascaris spp., Brugia malayi, Brugia timori,Bunostomum spp., Chabertia spp., Clonorchis spp., Cooperia spp.,Dicrocoelium spp, Dictyocaulus filaria, Diphyllobothrium latum,Dracunculus medinensis, Echinococcus granulosus, Echinococcusmultilocularis, Enterobius vermicularis, Faciola spp., Haemonchus spp.,Heterakis spp., Hymenolepis nana, Hyostrongulus spp., Loa Loa,Nematodirus spp., Oesophagostomum spp., Opisthorchis spp., Onchocercavolvulus, Ostertagia spp., Paragonimus spp., Schistosomen spp,Strongyloides fuelleborni, Strongyloides stercoralis, Stronyloides spp.,Taenia saginata, Taenia solium, Trichinella spiralis, Trichinellanativa, Trichinella britovi, Trichinella nelsoni, Trichinellapseudopsiralis, Trichostrongulus spp., Trichuris trichuria, Wuchereriabancrofti.

It is furthermore possible to control protozoans, such as Eimeria.

From the order of the Heteroptera, for example, Anasa tristis,Antestiopsis spp., Blissus spp., Calocoris spp., Campylomma livida,Cavelerius spp., Cimex spp., Collaria spp., Creontiades dilutus, Dasynuspiperis, Dichelops furcatus, Diconocoris hewetti, Dysdercus spp.,Euschistus spp., Eurygaster spp., Heliopeltis spp., Horcias nobilellus,Leptocorisa spp., Leptoglossus phyllopus, Lygus spp., Macropesexcavatus, Miridae, Monalonion atratum, Nezara spp., Oebalus spp.,Pentomidae, Piesma quadrata, Piezodorus spp., Psallus spp., Pseudacystapersea, Rhodnius spp., Sahlbergella singularis, Scaptocoris castanea,Scotinophora spp., Stephanitis nashi, Tibraca spp., Triatoma spp.

From the order of the Homoptera, for example, Acyrthosipon spp.,Acrogonia spp., Aeneolamia spp., Agonoscena spp., Aleurodes spp.,Aleurolobus barodensis, Aleurothrixus spp., Amrasca spp., Anuraphiscardui, Aonidiella spp., Aphanostigma piri, Aphis spp., Arboridiaapicalis, Aspidiella spp., Aspidiotus spp., Atanus spp., Aulacorthumsolani, Bemisia spp., Brachycaudus helichrysii, Brachycolus spp.,Brevicoryne brassicae, Calligypona marginata, Carneocephala fulgida,Ceratovacuna lanigera, Cercopidae, Ceroplastes spp., Chaetosiphonfragaefolii, Chionaspis tegalensis, Chlorita onukii, Chromaphisjuglandicola, Chrysomphalus ficus, Cicadulina mbila, Coccomytilus halli,Coccus spp., Cryptomyzus ribis, Dalbulus spp., Dialeurodes spp.,Diaphorina spp., Diaspis spp., Drosicha spp., Dysaphis spp., Dysmicoccusspp., Empoasca spp., Eriosoma spp., Erythroneura spp., Euscelisbilobatus, Ferrisia spp., Geococcus coffeae, Hieroglyphus spp.,Homalodisca coagulata, Hyalopterus arundinis, Icerya spp., Idiocerusspp., Idioscopus spp., Laodelphax striatellus, Lecanium spp.,Lepidosaphes spp., Lipaphis erysimi, Macrosiphum spp., Mahanarva spp.,Melanaphis sacchari, Metcalfiella spp., Metopolophium dirhodum, Monelliacostalis, Monelliopsis pecanis, Myzus spp., Nasonovia ribisnigri,Nephotettix spp., Nilaparvata lugens, Oncometopia spp., Ortheziapraelonga, Parabemisia myricae, Paratrioza spp., Parlatoria spp.,Pemphigus spp., Peregrinus maidis, Phenacoccus spp., Phloeomyzuspasserinii, Phorodon humuli, Phylloxera spp., Pinnaspis aspidistrae,Planococcus spp., Protopulvinaria pyriformis, Pseudaulacaspis pentagona,Pseudococcus spp., Psylla spp., Pteromalus spp., Pyrilla spp.,Quadraspidiotus spp., Quesada gigas, Rastrococcus spp., Rhopalosiphumspp., Saissetia spp., Scaphoides titanus, Schizaphis graminum,Selenaspidus articulatus, Sogata spp., Sogatella furcifera, Sogatodesspp., Stictocephala festina, Tenalaphara malayensis, Tinocalliscaryaefoliae, Tomaspis spp., Toxoptera spp., Trialeurodes spp., Triozaspp., Typhlocyba spp., Unaspis spp., Viteus vitifolii, Zygina spp.

From the order of the Hymenoptera, for example, Athalia spp., Diprionspp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.

From the order of the Isopoda, for example, Armadillidium vulgare,Oniscus asellus, Porcellio scaber.

From the order of the Isoptera, for example, Acromyrmex spp., Atta spp.,Cornitermes cumulans, Microtermes obesi, Odontotermes spp.,Reticulitermes spp.

From the order of the Lepidoptera, for example, Acronicta major,Adoxophyes spp., Aedia leucomelas, Agrotis spp., Alabama spp., Amyeloistransitella, Anarsia spp., Anticarsia spp., Argyroploce spp., Barathrabrassicae, Borbo cinnara, Bucculatrix thurberiella, Bupalus piniarius,Busseola spp., Cacoecia spp., Caloptilia theivora, Capua reticulana,Carpocapsa pomonella, Carposina niponensis, Chematobia brumata, Chilospp., Choristoneura spp., Clysia ambiguella, Cnaphalocerus spp.,Cnephasia spp., Conopomorpha spp., Conotrachelus spp., Copitarsia spp.,Cydia spp., Dalaca noctuides, Diaphania spp., Diatraea saccharalis,Earias spp., Ecdytolopha aurantium, Elasmopalpus lignosellus, Eldanasaccharina, Ephestia kuehniella, Epinotia spp., Epiphyas postvittana,Etiella spp., Eulia spp., Eupoecilia ambiguella, Euproctis spp., Euxoaspp., Feltia spp., Galleria mellonella, Gracillaria spp., Grapholithaspp., Hedylepta spp., Helicoverpa spp., Heliothis spp., Hofmannophilapseudospretella, Homoeosoma spp., Homona spp., Hyponomeuta padella,Kakivoria flavofasciata, Laphygma spp., Laspeyresia molesta, Leucinodesorbonalis, Leucoptera spp., Lithocolletis spp., Lithophane antennata,Lobesia spp., Loxagrotis albicosta, Lymantria spp., Lyonetia spp.,Malacosoma neustria, Maruca testulalis, Mamestra brassicae, Mocis spp.,Mythimna separata, Nymphula spp., Oiketicus spp., Oria spp., Orthagaspp., Ostrinia spp., Oulema oryzae, Panolis flammea, Parnara spp.,Pectinophora spp., Perileucoptera spp., Phthorimaea spp., Phyllocnistiscitrella, Phyllonorycter spp., Pieris spp., Platynota stultana, Plusiaspp., Plutella xylostella, Prays spp., Prodenia spp., Protoparce spp.,Pseudaletia spp., Pseudoplusia includens, Pyrausta nubilalis,Rachiplusia nu, Schoenobius spp., Scirpophaga spp., Scotia segetum,Sesamia spp., Sparganothis spp., Spodoptera spp., Stathmopoda spp.,Stomopteryx subsecivella, Synanthedon spp., Tecia solanivora, Thermesiagemmatalis, Tinea pellionella, Tineola bisselliella, Tortrix spp.,Trichoplusia spp., Tuta absoluta, Virachola spp.

From the order of the Orthoptera, for example, Acheta domesticus, Blattaorientalis, Blattella germanica, Dichroplus spp., Gryllotalpa spp.,Leucophaea maderae, Locusta spp., Melanoplus spp., Periplanetaamericana, Schistocerca gregaria.

From the order of the Siphonaptera, for example, Ceratophyllus spp.,Xenopsylla cheopis.

From the order of the Symphyla, for example, Scutigerella spp.

From the order of the Thysanoptera, for example, Anaphothrips obscurus,Baliothrips biformis, Drepanothris reuteri, Enneothrips flavens,Frankliniella spp., Heliothrips spp., Hercinothrips femoralis,Rhipiphorothrips cruentatus, Scirtothrips spp., Taeniothrips cardamoni,Thrips spp.

From the order of the Thysanura, for example, Lepisma saccharina.

The plant-parasitic nematodes include, for example, Aphelenchoides spp.,Bursaphelenchus spp., Ditylenchus spp., Globodera spp., Heterodera spp.,Longidorus spp., Meloidogyne spp., Pratylenchus spp., Radopholussimilis, Trichodorus spp., Tylenchulus semipenetrans, Xiphinema spp.

If appropriate, the compounds according to the invention can, at certainconcentrations or application rates, also be used as herbicides,safeners, growth regulators or agents to improve plant properties, or asmicrobicides, for example as fungicides, antimycotics, bactericides,viricides (including agents against viroids) or as agents against MLO(Mycoplasma-like organisms) and RLO (Rickettsia-like organisms). Ifappropriate, they can also be employed as intermediates or precursorsfor the synthesis of other active compounds.

The active compounds can be converted to the customary formulations,such as solutions, emulsions, wettable powders, water- and oil-basedsuspensions, powders, dusts, pastes, soluble powders, soluble granules,granules for broadcasting, suspension-emulsion concentrates, naturalmaterials impregnated with active compound, synthetic materialsimpregnated with active compound, fertilizers and microencapsulations inpolymeric substances.

These formulations are produced in a known manner, for example by mixingthe active compounds with extenders, that is liquid solvents and/orsolid carriers, optionally with the use of surfactants, that isemulsifiers and/or dispersants and/or foam-formers. The formulations areprepared either in suitable plants or else before or during theapplication.

Suitable for use as auxiliaries are substances which are suitable forimparting to the composition itself and/or to preparations derivedtherefrom (for example spray liquors, seed dressings) particularproperties such as certain technical properties and/or also particularbiological properties. Typical suitable auxiliaries are: extenders,solvents and carriers.

Suitable extenders are, for example, water, polar and nonpolar organicchemical liquids, for example from the classes of the aromatic andnon-aromatic hydrocarbons (such as paraffins, alkylbenzenes,alkylnaphthalenes, chlorobenzenes), the alcohols and polyols (which, ifappropriate, may also be substituted, etherified and/or esterified), theketones (such as acetone, cyclohexanone), esters (including fats andoils) and (poly)ethers, the unsubstituted and substituted amines,amides, lactams (such as N-alkylpyrrolidones) and lactones, thesulphones and sulphoxides (such as dimethyl sulphoxide).

If the extender used is water, it is also possible to employ, forexample, organic solvents as auxiliary solvents. Essentially, suitableliquid solvents are: aromatics such as xylene, toluene oralkylnaphthalenes, chlorinated aromatics and chlorinated aliphatichydrocarbons such as chlorobenzenes, chloroethylenes or methylenechloride, aliphatic hydrocarbons such as cyclohexane or paraffins, forexample petroleum fractions, mineral and vegetable oils, alcohols suchas butanol or glycol and also their ethers and esters, ketones such asacetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone,strongly polar solvents such as dimethyl sulphoxide, and also water.

According to the invention, a carrier is a natural or synthetic organicor inorganic substance which may be solid or liquid and with which theactive compounds are mixed or bonded for better applicability, inparticular for application to plants or parts of plants. The solid orliquid carrier is generally inert and should be suitable for use inagriculture.

Suitable solid carriers are:

for example, ammonium salts and ground natural minerals such as kaolins,clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceousearth, and ground synthetic minerals, such as finely divided silica,alumina and silicates; suitable solid carriers for granules are: forexample, crushed and fractionated natural rocks such as calcite, marble,pumice, sepiolite and dolomite, and also synthetic granules of inorganicand organic meals, and granules of organic material such as paper,sawdust, coconut shells, maize cobs and tobacco stalks; suitableemulsifiers and/or foam-formers are: for example, nonionic and anionicemulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylenefatty alcohol ethers, for example alkylaryl polyglycol ethers,alkylsulphonates, alkyl sulphates, arylsulphonates and also proteinhydrolysates; suitable dispersants are nonionic and/or ionic substances,for example from the classes of the alcohol-POE and/or -POP ethers, acidand/or POP-POE esters, alkylaryl and/or POP-POE ethers, fat- and/orPOP-POE adducts, POE- and/or POP-polyol derivatives, POE- and/orPOP-sorbitan or -sugar adducts, alkyl or aryl sulphates, alkyl- orarylsulphonates and alkyl or aryl phosphates or the correspondingPO-ether adducts. Furthermore, suitable oligo- or polymers, for examplethose derived from vinylic monomers, from acrylic acid, from EO and/orPO alone or in combination with, for example, (poly)alcohols or(poly)amines. It is also possible to employ lignin and its sulphonicacid derivatives, unmodified and modified celluloses, aromatic and/oraliphatic sulphonic acids and their adducts with formaldehyde.

Tackifiers such as carboxymethylcellulose and natural and syntheticpolymers in the form of powders, granules or latices, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, as well as naturalphospholipids such as cephalins and lecithins, and syntheticphospholipids, can be used in the formulations.

It is possible to use colorants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian Blue, and organic dyestuffs,such as alizarin dyestuffs, azo dyestuffs and metal phthalocyaninedyestuffs, and trace nutrients such as salts of iron, manganese, boron,copper, cobalt, molybdenum and zinc.

Other possible additives are perfumes, mineral or vegetable, optionallymodified oils, waxes and nutrients (including trace nutrients), such assalts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.

Stabilizers, such as low-temperature stabilizers, preservatives,antioxidants, light stabilizers or other agents which improve chemicaland/or physical stability may also be present.

The formulations generally comprise between 0.01 and 98% by weight ofactive compound, preferably between 0.5 and 90%.

The active compound according to the invention can be used in itscommercially available formulations and in the use forms, prepared fromthese formulations, as a mixture with other active compounds, such asinsecticides, attractants, sterilizing agents, bactericides, acaricides,nematicides, fungicides, growth-regulating substances, herbicides,safeners, fertilizers or semiochemicals.

A mixture with other known active compounds, such as herbicides,fertilizers, growth regulators, safeners, semiochemicals, or else withagents for improving the plant properties, is also possible.

When used as insecticides, the active compounds according to theinvention can furthermore be present in their commercially availableformulations and in the use forms, prepared from these formulations, asa mixture with synergists. Synergists are compounds which increase theaction of the active compounds, without it being necessary for thesynergist added to be active itself.

When used as insecticides, the active compounds according to theinvention can furthermore be present in their commercially availableformulations and in the use forms, prepared from these formulations, asa mixture with inhibitors which reduce degradation of the activecompound after use in the environment of the plant, on the surface ofparts of plants or in plant tissues.

The active compound content of the use forms prepared from thecommercially available formulations can vary within wide limits. Theactive compound concentration of the use forms can be from 0.00000001 to95% by weight of active compound, preferably between 0.00001 and 1% byweight.

The compounds are employed in a customary manner appropriate for the useforms.

All plants and plant parts can be treated in accordance with theinvention. Plants are to be understood as meaning in the present contextall plants and plant populations such as desired and undesired wildplants or crop plants (including naturally occurring crop plants). Cropplants can be plants which can be obtained by conventional plantbreeding and optimization methods or by biotechnological and geneticengineering methods or by combinations of these methods, including thetransgenic plants and including the plant cultivars protectable or notprotectable by plant breeders' rights. Plant parts are to be understoodas meaning all parts and organs of plants above and below the ground,such as shoot, leaf, flower and root, examples which may be mentionedbeing leaves, needles, stalks, stems, flowers, fruit bodies, fruits,seeds, roots, tubers and rhizomes. The plant parts also includeharvested material, and vegetative and generative propagation material,for example cuttings, tubers, rhizomes, offshoots and seeds.

Treatment according to the invention of the plants and plant parts withthe active compounds is carried out directly or by allowing thecompounds to act on their surroundings, habitat or storage space by thecustomary treatment methods, for example by immersion, spraying,evaporation, fogging, scattering, painting on, injection and, in thecase of propagation material, in particular in the case of seeds, alsoby applying one or more coats.

As already mentioned above, it is possible to treat all plants and theirparts according to the invention. In a preferred embodiment, wild plantspecies and plant cultivars, or those obtained by conventionalbiological breeding methods, such as crossing or protoplast fusion, andparts thereof, are treated. In a further preferred embodiment,transgenic plants and plant cultivars obtained by genetic engineeringmethods, if appropriate in combination with conventional methods(Genetically Modified Organisms), and parts thereof are treated. Theterms “parts”, “parts of plants” and “plant parts” have been explainedabove.

Particularly preferably, plants of the plant cultivars which are in eachcase commercially available or in use are treated according to theinvention. Plant cultivars are to be understood as meaning plants havingnovel properties (“traits”) which have been obtained by conventionalbreeding, by mutagenesis or by recombinant DNA techniques. These can becultivars, bio- or genotypes.

Depending on the plant species or plant cultivars, their location andgrowth conditions (soils, climate, vegetation period, diet), thetreatment according to the invention may also result in superadditive(“synergistic”) effects. Thus, for example, reduced application ratesand/or a widening of the activity spectrum and/or an increase in theactivity of the substances and compositions which can be used accordingto the invention, better plant growth, increased tolerance to high orlow temperatures, increased tolerance to drought or to water or soilsalt content, increased flowering performance, easier harvesting,accelerated maturation, higher harvest yields, higher quality and/or ahigher nutritional value of the harvested products, better storagestability and/or processability of the harvested products are possible,which exceed the effects which were actually to be expected.

The transgenic plants or plant cultivars (obtained by geneticengineering) which are preferably to be treated according to theinvention include all plants which, by virtue of the geneticmodification, received genetic material which imparted particularlyadvantageous, useful traits to these plants. Examples of such traits arebetter plant growth, increased tolerance to high or low temperatures,increased tolerance to drought or to water or soil salt content,increased flowering performance, easier harvesting, acceleratedmaturation, higher harvest yields, higher quality and/or a highernutritional value of the harvested products, better storage stabilityand/or processability of the harvested products. Further andparticularly emphasized examples of such traits are a better defence ofthe plants against animal and microbial pests, such as against insects,mites, phytopathogenic fungi, bacteria and/or viruses, and alsoincreased tolerance of the plants to certain herbicidally activecompounds. Examples of transgenic plants which may be mentioned are theimportant crop plants, such as cereals (wheat, rice), maize, soya beans,potatoes, sugar beet, tomatoes, peas and other vegetable varieties,cotton, tobacco, oilseed rape and also fruit plants (with the fruitsapples, pears, citrus fruits and grapes), and particular emphasis isgiven to maize, soya beans, potatoes, cotton, tobacco and oilseed rape.Traits that are emphasized are in particular increased defence of theplants against insects, arachnids, nematodes and slugs and snails byvirtue of toxins formed in the plants, in particular those formed in theplants by the genetic material from Bacillus thuringiensis (for exampleby the genes CryIA(a), CryIA(b), CryIA(c), CryIIA, CryIIIA, CryIIIB2,Cry9c, Cry2Ab, Cry3Bb and CryIF and also combinations thereof) (referredto hereinbelow as “Bt plants”). Traits that are also particularlyemphasized are the increased defence of the plants against fungi,bacteria and viruses by systemic acquired resistance (SAR), systemin,phytoalexins, elicitors and resistance genes and correspondinglyexpressed proteins and toxins. Traits that are furthermore particularlyemphasized are the increased tolerance of the plants to certainherbicidally active compounds, for example imidazolinones,sulphonylureas, glyphosate or phosphinotricin (for example the “PAT”gene). The genes which impart the desired traits in question can also bepresent in combination with one another in the transgenic plants.Examples of “Bt plants” which may be mentioned are maize varieties,cotton varieties, soya bean varieties and potato varieties which aresold under the trade names YIELD GARD® (for example maize, cotton, soyabeans), KnockOut® (for example maize), StarLink® (for example maize),Bollgard® (cotton), Nucotn® (cotton) and NewLeaf® (potato). Examples ofherbicide-tolerant plants which may be mentioned are maize varieties,cotton varieties and soya bean varieties which are sold under the tradenames Roundup Ready® (tolerance to glyphosate, for example maize,cotton, soya bean), Liberty Link® (tolerance to phosphinotricin, forexample oilseed rape), IMI® (tolerance to imidazolinones) and STS®(tolerance to sulphonylureas, for example maize). Herbicide-resistantplants (plants bred in a conventional manner for herbicide tolerance)which may be mentioned include the varieties sold under the nameClearfield® (for example maize). Of course, these statements also applyto plant cultivars having these genetic traits or genetic traits stillto be developed, which plant cultivars will be developed and/or marketedin the future.

The plants listed can be treated according to the invention in aparticularly advantageous manner with the compounds of the generalformula (I) or the active compound mixtures according to the invention.The preferred ranges stated above for the active compounds or mixturesalso apply to the treatment of these plants. Particular emphasis isgiven to the treatment of plants with the compounds or mixturesspecifically mentioned in the present text.

The compounds of the formula (I) according to the invention (activecompounds) have excellent herbicidal activity against a broad spectrumof economically important monocotylidonous and dicotylidonous annualharmful plants. The active compounds also act efficiently on perennialharmful plants which produce shoots from rhizomes, root stocks or otherperennial organs and which are difficult to control.

The amount of active compound used may vary within a relatively widerange. It depends essentially on the nature of the desired effect. Ingeneral, the application rates are between 1 g and 10 kg of activecompound per hectare of soil area, preferably between 5 g and 5 kg perha.

The advantageous effect of the compatibility with crop plants of theactive compound combinations according to the invention is particularlypronounced at certain concentration ratios. However, the weight ratiosof the active compounds in the active compound combinations can bevaried within relatively wide ranges. In general, from 0.001 to 1000parts by weight, preferably from 0.01 to 100 parts by weight,particularly preferably from 0.05 to 20 parts by weight, of one of thecrop plant compatibility-improving compounds (antidotes/safeners)mentioned above under (b′) are present per part by weight of activecompound of the formula (I).

The active compound combinations according to the invention aregenerally applied in the form of finished formulations. However, theactive compounds present in the active compound combinations can, asindividual formulations, also be mixed during use, i.e. be applied inthe form of tank mixtures.

For certain applications, in particular in the post-emergence method, itmay furthermore be advantageous to include in the formulations, asfurther additives, mineral or vegetable oils which are tolerated byplants (for example the commercial preparation “Rako Binol”), orammonium salts, such as, for example, ammonium sulphate or ammoniumthiocyanate.

The novel active compound combinations can be used as such, in the formof their formulations or the use forms prepared therefrom by furtherdilution, such as ready-to-use solutions, suspensions, emulsions,powders, pastes and granules. The application is in the customarymanner, for example by watering, spraying, atomizing, dusting orbroadcasting.

The application rates of the active compound combinations according tothe invention can be varied within a certain range; they depend, interalia, on the weather and on soil factors. In general, the applicationrates are from 0.001 to 5 kg per ha, preferably from 0.005 to 2 kg perha, particularly preferably from 0.01 to 0.5 kg per ha.

Depending on their properties, the safeners to be used according to theinvention can be used for pretreating the seed of the crop plant (seeddressing) or can be introduced into the seed ferrules prior to the seedor be used separately prior to the herbicide or together with theherbicide, before or after emergence of the plants.

Examples of plants which may be mentioned are important crop plants,such as cereals (wheat, barley, rice), maize, soya beans, potatoes,cotton, oilseed rape, beet, sugar cane and also fruit plants (with thefruits apples, pears, citrus fruits and grapevines), greater emphasisbeing given to cereals, maize, soya beans, potatoes, cotton and oilseedrape.

All plants and plant parts can be treated with the active compoundsaccording to the invention. Here, plants are to be understood as meaningall plants and plant populations such as wanted and unwanted wild plantsor crop plants (including naturally occurring crop plants). Crop plantscan be plants which can be obtained by conventional plant breeding andoptimization methods or by biotechnological and recombinant methods orby combinations of these methods, including the transgenic plants andinclusive of the plant cultivars protectable or not protectable by plantbreeders rights. Plant parts are to be understood as meaning all partsand organs of plants above and below the ground, such as shoot, leaf,flower and root, examples which may be mentioned being leaves, needles,stalks, stems, flowers, fruit bodies, fruits and seed and also roots,tubers and rhizomes. The plant parts also include harvested material,and also vegetative and generative propagation material, for examplecuttings, tubers, rhizomes, offshoots and seeds.

Treatment according to the invention of the plants and plant parts withthe active compounds is carried out directly or by allowing thecompounds to act on their surroundings, habitat or storage space by thecustomary treatment methods, for example by immersion, spraying,evaporation, fogging, broadcasting, painting on or injection and, in thecase of propagation material, in particular in the case of seed, also byapplying one or more coats.

The present invention therefore also relates to a method of controllingunwanted plants or for regulating the growth of plants, preferably incrops of plants, where one or more compound(s) according to theinvention is/are applied to the plants (for example harmful plants suchas monocotyledonous or dicotyledonous weeds or unwanted crop plants), tothe seed (for example grains, seeds or vegetative propagules such astubers or shoot parts with buds) or to the area on which the plants grow(for example the area under cultivation). In this context, the compoundsaccording to the invention can be applied for example pre-planting (ifappropriate also by incorporation into the soil), pre-emergence orpost-emergence. Examples of individual representatives of themonocotyledonous and dicotyledonous weed flora which can be controlledby the compounds according to the invention shall be mentioned, withoutthe mention being intended as a limitation to certain species.

Monocotyledonous Harmful Plants of the Genera:

Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria,Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium,Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa,Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa,Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa,Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum.

Dicotyledonous Weeds of the Genera:

Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Artemisia,Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea,Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum,Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia,Lamium, Lepidium, Lindernia, Matricaria, Mentha, Mercurialis, Mullugo,Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca,Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senecio,Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria,Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium.

The plants listed can be treated according to the invention in aparticularly advantageous manner with the compounds of the generalformula (I) or the active compound mixtures according to the invention.The preferred ranges stated above for the active compounds or mixturesalso apply to the treatment of these plants. Particular emphasis isgiven to the treatment of plants with the compounds or mixturesspecifically mentioned in the present text.

If the compounds according to the invention are applied to the soilsurface before germination, either the emergence of the weed seedlingsis prevented completely or the weeds grow until they have reached thecotyledon stage, but then stop their growth and, finally, die completelyafter three to four weeks have elapsed.

When the active compounds are applied post-emergence to the green plantparts, growth stops after the treatment, and the harmful plants remainin the growth stage of the time of application or die fully after acertain period of time, so that competition by weeds, which is harmfulto the crop plants, is thus eliminated at an early point in time and ina sustained manner.

Although the compounds according to the invention display an outstandingherbicidal activity against monocotyledonous and dicotyledonous weeds,crop plants of economically important crops, for example dicotyledonouscrops of the genera Arachis, Beta, Brassica, Cucumis, Cucurbita,Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum,Lycopersicon, Miscanthus, Nicotiana, Phaseolus, Pisum, Solanum, Vicia,or monocotyledonous crops of the genera Allium, Ananas, Asparagus,Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale,Triticum, Zea, are damaged only to an insignificant extent, or not atall, depending on the structure of the respective compound according tothe invention and its application rate. This is why the presentcompounds are highly suitable for the selective control of unwantedvegetation in plant crops such as agriculturally useful plants orornamentals.

Moreover, the compounds according to the invention (depending on theirrespective structure and the application rate applied) have outstandinggrowth-regulatory properties in crop plants. They engage in the plantmetabolism in a regulatory fashion and can therefore be employed for theinfluencing, in a targeted manner, of plant constituents and forfacilitating harvesting, such as, for example, by triggering desiccationand stunted growth. Moreover, they are also suitable for generallycontrolling and inhibiting unwanted vegetative growth without destroyingthe plants in the process. Inhibiting the vegetative growth plays animportant role in many monocotyledonous and dicotyledonous crops sincefor example lodging can be reduced, or prevented completely, hereby.

As already mentioned above, it is possible to treat all plants and theirparts according to the invention. In a preferred embodiment, wild plantspecies and plant cultivars, or those obtained by conventionalbiological breeding methods, such as crossing or protoplast fusion, andparts thereof, are treated. In a further preferred embodiment,transgenic plants and plant cultivars obtained by genetic engineeringmethods, if appropriate in combination with conventional methods(Genetically Modified Organisms), and parts thereof are treated. Theterms “parts”, “parts of plants” and “plant parts” have been explainedabove.

Particularly preferably, plants of the plant cultivars which are in eachcase commercially available or in use are treated according to theinvention. Plant cultivars are to be understood as meaning plants havingnovel properties (“traits”) which have been obtained by conventionalbreeding, by mutagenesis or by recombinant DNA techniques. These can becultivars, bio- or genotypes.

Depending on the plant species or plant cultivars, their location andgrowth conditions (soils, climate, vegetation period, diet), thetreatment according to the invention may also result in superadditive(“synergistic”) effects. Thus, for example, reduced application ratesand/or a widening of the activity spectrum and/or an increase in theactivity of the substances and compositions which can be used accordingto the invention, better plant growth, increased tolerance to high orlow temperatures, increased tolerance to drought or to water or soilsalt content, increased flowering performance, easier harvesting,accelerated maturation, higher harvest yields, higher quality and/or ahigher nutritional value of the harvested products, better storagestability and/or processability of the harvested products are possible,which exceed the effects which were actually to be expected.

Owing to their herbicidal and plant-growth-regulatory properties, theactive compounds can also be employed for controlling harmful plants incrops of known genetically modified plants or genetically modifiedplants which are still to be developed. As a rule, the transgenic plantsare distinguished by especially advantageous properties, for example byresistances to certain pesticides, mainly certain herbicides,resistances to plant diseases or causative organisms of plant diseases,such as certain insects or microorganisms such as fungi, bacteria orviruses. Other special properties relate for example to the harvestedmaterial with regard to quantity, quality, storability, composition andspecific constituents. Thus, transgenic plants with an increased starchcontent or a modified starch quality or those with a different fattyacid composition of the harvested material are known. Further particularproperties may be tolerance or resistance to abiotec stresses, forexample heat, cold, drought, salt and ultraviolet radiation.

It is preferred to use the compounds of the formula (I) according to theinvention in economically important transgenic crops of useful plantsand ornamentals, for example of cereals such as wheat, barley, rye,oats, sorghum and millet, rice, cassava and maize or else crops of sugarbeet, cotton, soya bean, oilseed rape, potato, tomato, peas and othervegetables.

It is preferred to employ the compounds of the formula (I) as herbicidesin crops of useful plants which are resistant, or have been maderesistant by recombinant means, to the phytotoxic effects of theherbicides.

Conventional ways of generating novel plants which, in comparison withexisting plants, have modified properties are, for example, traditionalbreeding methods and the generation of mutants. Alternatively, novelplants with modified properties can be generated with the aid ofrecombinant methods (see, for example, EP-A-0221044, EP-A-0131624). Forexample, the following have been described in several cases:

-   -   recombinant modifications of crop plants for the purposes of        modifying the starch synthesized in the plants (for example WO        92/11376, WO 92/14827, WO 91/19806),    -   transgenic crop plants which are resistant to certain herbicides        of the glufosinate type (cf., for example, EP-A-0242236,        EP-A-242246) or of the glyphosate type (WO 92/00377) or of the        sulphonylurea type (EP-A-0257993, U.S. Pat. No. 5,013,659),    -   transgenic crop plants, for example cotton, which is capable of        producing Bacillus thuringiensis toxins (Bt toxins), which make        the plants resistant to certain pests (EP-A-0142924,        EP-A-0193259),    -   transgenic crop plants with a modified fatty acid composition        (WO 91/13972),    -   genetically modified crop plants with novel constituents or        secondary metabolites, for example novel phytoalexins, which        bring about an increased disease resistance (EPA 309862,        EPA0464461),    -   genetically modified plants with reduced photorespiration which        feature higher yields and higher stress tolerance (EPA 0305398),    -   transgenic crop plants which produce pharmaceutically or        diagnostically important proteins (“molecular pharming”),    -   transgenic crop plants which are distinguished by higher yields        or better quality,    -   transgenic crop plants which are distinguished by a combination,        for example of the abovementioned novel properties (“gene        stacking”).

A large number of molecular-biological techniques by means of whichnovel transgenic plants with modified properties can be generated areknown in principle; see, for example, I. Potrykus and G. Spangenberg(eds.) Gene Transfer to Plants, Springer Lab Manual (1995), SpringerVerlag Berlin, Heidelberg. or Christou, “Trends in Plant Science” 1(1996) 423-431.

To carry out such recombinant manipulations, it is possible to introducenucleic acid molecules into plasmids, which permit a mutagenesis orsequence modification by recombination of DNA sequences. For example,base substitutions can be carried out, part-sequences can be removed, ornatural or synthetic sequences may be added with the aid of standardmethods. To link the DNA fragments with one another, it is possible toadd adapters or linkers to the fragments; see, for example, Sambrook etal., 1989, Molecular Cloning, A Laboratory Manual, 2nd ed., Cold SpringHarbor Laboratory Press, Cold Spring Harbor, N.Y.; or Winnacker “Geneand Klone”, VCH Weinheim 2nd ed., 1996

The generation of plant cells with a reduced activity for a gene productcan be achieved for example by the expression of at least onecorresponding antisense RNA, a sense RNA for achieving a cosuppressioneffect or by the expression of at least one correspondingly constructedribozyme, which specifically cleaves transcripts of the abovementionedgene product.

To this end, it is possible firstly to use DNA molecules which compriseall of the coding sequence of a gene product, including any flankingsequences which may be present, or else DNA molecules which onlycomprise parts of the coding sequence, it being necessary for theseparts to be long enough to bring about an antisense effect in the cells.It is also possible to use DNA sequences which have a high degree ofhomology with the coding sequences of a gene product, but which are notentirely identical.

When expressing nucleic acid molecules in plants, the proteinsynthesized may be localized in any compartment of the plant cell. Inorder to achieve localization in a particular compartment, however, itis possible for example to link the coding region to DNA sequences whichensure the localization in a specific compartment. Such sequences areknown to the skilled worker (see, for example, Braun et al., EMBO J. 11(1992), 3219-3227; Wolter et al., Proc. Natl. Acad. Sci. USA 85 (1988),846-850; Sonnewald et al., Plant J. 1 (1991), 95-106). The nucleic acidmolecules can also be expressed in the organelles of the plant cells.

The transgenic plant cells can be regenerated by known techniques togive intact plants. In principle, the transgenic plants may be plants ofany plant species, that is to say both monocotyledonous anddicotyledonous plants.

Thus, transgenic plants can be obtained which feature modifiedproperties as the result of overexpression, suppression or inhibition ofhomologous (=natural) genes or gene sequences or expression ofheterologous (=foreign) genes or gene sequences.

It is preferred to employ the compounds (I) according to the inventionin transgenic crops which are resistant to growth regulators such as,for example, dicamba, or to herbicides which inhibit essential plantenzymes, for example acetolactate synthases (ALS), EPSP synthases,glutamine synthases (GS) or hydroxyphenylpyruvate dioxygenases (HPPD),or to herbicides from the group of the sulphonylureas, glyphosate,glufosinate or benzoylisoxazoles and analogous active compounds.

When the active compounds according to the invention are used intransgenic crops, effects are frequently observed—in addition to theeffects on harmful plants which can be observed in other crops—which arespecific for the application in the transgenic crop in question, forexample a modified or specifically widened spectrum of weeds which canbe controlled, modified application rates which may be employed forapplication, preferably good combinability with the herbicides to whichthe transgenic crop is resistant, and an effect on growth and yield ofthe transgenic crop plants.

The invention therefore also relates to the use of the compounds of theformula (I) according to the invention as herbicides for controllingharmful plants in transgenic crop plants.

The compounds according to the invention can be used in the form ofwettable powders, emulsifiable concentrates, sprayable solutions,dusting products or granules in the customary formulations. Theinvention therefore also provides herbicidal and plant growth-regulatingcompositions which comprise the compounds according to the invention.

The compounds according to the invention can be formulated in variousways according to which biological and/or physicochemical parameters arerequired. Possible formulations include, for example: wettable powders(WP), water-soluble powders (SP), water-soluble concentrates,emulsifiable concentrates (EC), emulsions (EW) such as oil-in-water andwater-in-oil emulsions, sprayable solutions, suspension concentrates(SC), oil- or water-based dispersions, oil-miscible solutions, capsulesuspensions (CS), dusting products (DP), seed-dressing products,granules for scattering and soil application, granules (GR) in the formof microgranules, spray granules, coated granules and adsorptiongranules, water-dispersible granules (WG), water-soluble granules (SG),ULV formulations, microcapsules and waxes.

These individual formulation types are known in principle and aredescribed, for example, in: Winnacker-Küchler, “Chemische Technologie”[Chemical technology], Volume 7, C. Hanser Verlag Munich, 4th Ed. 1986,Wade van Valkenburg, “Pesticide Formulations”, Marcel Dekker, N.Y.,1973; K. Martens, “Spray Drying” Handbook, 3rd Ed. 1979, G. Goodwin Ltd.London.

The necessary formulation assistants, such as inert materials,surfactants, solvents and further additives, are likewise known and aredescribed, for example, in: Watkins, “Handbook of Insecticide DustDiluents and Carriers”, 2nd Ed., Darland Books, Caldwell N.J., H. v.Olphen, “Introduction to Clay Colloid Chemistry”; 2nd Ed., J. Wiley &Sons, N.Y.; C. Marsden, “Solvents Guide”; 2nd Ed., Interscience, N.Y.1963; McCutcheon's “Detergents and Emulsifiers Annual”, MC Publ. Corp.,Ridgewood N.J.; Sisley and Wood, “Encyclopedia of Surface ActiveAgents”, Chem. Publ. Co. Inc., N.Y. 1964; Schönfeldt,“Grenzflächenaktive Äthylenoxidaddukte” [Interface-active ethylene oxideadducts], Wiss. Verlagsgesell, Stuttgart 1976; Winnacker-Küchler,“Chemische Technologie”, Volume 7, C. Hanser Verlag Munich, 4th Ed.1986.

Based on these formulations, it is also possible to prepare combinationswith other pesticidally active compounds, such as, for example,insecticides, acaracides, berbicides, fungicides, and also withsafeners, fertilizers and/or growth regulators, for example in the formof a finished formulation or as a tank mix.

Wettable powders are preparations which can be dispersed uniformly inwater and, as well as the active compound, apart from a diluent or inertsubstance, also comprise surfactants of the ionic and/or nonionic type(wetting agents, dispersants), for example polyoxyethylatedalkylphenols, polyoxyethylated fatty alcohols, polyoxyethylated fattyamines, fatty alcohol polyglycol ether sulphates, alkanesulphonates,alkylbenzenesulphonates, sodium lignosulphonate, sodium2,2′-dinaphthylmethane-6,6′-disulphonate, sodiumdibutylnaphthalenesulphonate or else sodium oleylmethyltauride. Toprepare the wettable powders, the active herbicidal compounds are groundfinely, for example in customary apparatus such as hammer mills, blowermills and air-jet mills and simultaneously or subsequently mixed withthe formulation assistants.

Emulsifiable concentrates are prepared by dissolving the active compoundin an organic solvent, for example butanol, cyclohexanone,dimethylformamide, xylene or else relatively high-boiling aromatics orhydrocarbons or mixtures of the organic solvents with addition of one ormore surfactants of the ionic and/or nonionic type (emulsifiers). Theemulsifiers used may, for example, be: calcium alkylarylsulphonates suchas calcium dodecylbenzenesulphonate, or nonionic emulsifiers such asfatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcoholpolyglycol ethers, propylene oxide-ethylene oxide condensation products,alkyl polyethers, sorbitan esters, for example sorbitan fatty acidesters, or polyoxyethylene sorbitan esters, for example polyoxyethylenesorbitan fatty acid esters.

Dusting products are obtained by grinding the active compound withfinely divided solid substances, for example talc, natural clays such askaolin, bentonite and pyrophyllite, or diatomaceous earth.

Suspension concentrates may be water- or oil-based. They may beprepared, for example, by wet grinding by means of commercial bead millsand optional addition of surfactants as have, for example, already beenlisted above for the other formulation types.

Emulsions, for example oil-in-water emulsions (EW), can be prepared, forexample, by means of stirrers, colloid mills and/or static mixers usingaqueous organic solvents and optionally surfactants, as have, forexample, already been listed above for the other formulation types.

Granules can be produced either by spraying the active compound ontoadsorptive granulated inert material or by applying active compoundconcentrates by means of adhesives, for example polyvinyl alcohol,sodium polyacrylate or else mineral oils, onto the surface of carrierssuch as sand, kaolinites or of granulated inert material. It is alsopossible to granulate suitable active compounds in the manner customaryfor the production of fertilizer granules—if desired in a mixture withfertilizers.

Water-dispersible granules are prepared generally by the customaryprocesses such as spray-drying, fluidized bed granulation, pangranulation, mixing with high-speed mixers and extrusion without solidinert material.

For the preparation of pan, fluidized bed, extruder and spray granules,see, for example, processes in “Spray-Drying Handbook” 3rd ed. 1979, G.Goodwin Ltd., London; J. E. Browning, “Agglomeration”, Chemical andEngineering 1967, pages 147 ff; “Perry's Chemical Engineer's Handbook”,5th Ed., McGraw-Hill, New York 1973, pp. 8-57.

For further details regarding the formulation of crop protectioncompositions, see, for example, G. C. Klingman, “Weed Control as aScience”, John Wiley and Sons, Inc., New York, 1961, pages 81-96 and J.D. Freyer, S. A. Evans, “Weed Control Handbook”, 5th Ed., BlackwellScientific Publications, Oxford, 1968, pages 101-103.

The agrochemical formulations contain generally from 0.1 to 99% byweight, in particular from 0.1 to 95% by weight, of compounds accordingto the invention.

In wettable powders, the active compound concentration is, for example,from about 10 to 90% by weight; the remainder to 100% by weight consistsof customary formulation constituents. In the case of emulsifiableconcentrates, the active compound concentration may be from about 1 to90% by weight, preferably from 5 to 80% by weight. Dust-typeformulations contain from 1 to 30% by weight of active compound,preferably usually from 5 to 20% by weight of active compound; sprayablesolutions contain from about 0.05 to 80% by weight, preferably from 2 to50% by weight of active compound. In water-dispersible granules, theactive compound content depends partly on whether the active compound ispresent in solid or liquid form and which granulation assistants,fillers, etc. are used. In the granules dispersible in water, thecontent of active compound is, for example, between 1 and 95% by weight,preferably between 10 and 80% by weight.

In addition, the active compound formulations mentioned optionallycomprise the respective customary adhesives, wetting agents,dispersants, emulsifiers, penetrants, preservatives, antifreeze agentsand solvents, fillers, carriers and dyes, defoamers, evaporationinhibitors and agents which influence the pH and the viscosity.

The term “active compounds” or “compounds” in each case also includesthe active compound combinations mentioned herein.

The preparation and the use of the active compounds according to theinvention is illustrated by the examples below.

PREPARATION EXAMPLES Examples I-a-0 and I-a-13-(Benzyloxy)-2-(2,6-diethyl-4-methylphenyl)-5-methylene-4,5,6,6a-tetrahydropentalen-1(3aH)-oneand3-(benzyloxy)-2-(2,6-diethyl-4-methylphenyl)-5-(hydroxymethyl)-4,5,6,6a-tetrahydropentalen-1(3aH)-one

6.80 g (22.94 mmol) of2-(2,6-diethyl-4-methylphenyl)-3-hydroxy-5-methylene-4,5,6,6a-tetrahydropentalen-1(3aH)-one(Preparation Example I-a-5 known from WO 2010/040460), 8.71 g (68.82mmol) of benzyl chloride and 9.51 g of potassium carbonate in 50 ml ofacetone are heated at reflux for 2 h, the solvent is then distilled offand the residue is chromatographed on silica gel using ethylacetate/hexane 1:4. This gives 6.40 g (72%) of3-(benzyloxy)-2-(2,6-diethyl-4-methylphenyl)-5-methylene-4,5,6,6a-tetrahydropentalen-1(3aH)-onein the form of colourless crystals of m.p. 87-88° C.

¹H-NMR (400 MHz, CDCl₃): δ=1.03 and 1.12 (in each case t, in each case3H), 3.03 and 3.37 (in each case mc, in each case 1H), AB system:δ_(A)=4.73, δ_(B)=4.79, J=13 Hz (benzyl-CH ₂), 4.90 (mc, 2H), 6.88 and7.12 (in each case mc, in each case 2H), 7.32 (mc, 3H)

Over a period of 30 min, 17 ml of borane/THF (tetrahydrofuran) complex(1 molar solution, 17 mmol) are added dropwise to 6.00 g (15.52 mmol) of3-(benzyloxy)-2-(2,6-diethyl-4-methylphenyl)-5-methylene-4,5,6,6a-tetrahydropentalen-1(3aH)-onein 100 ml of THF, and the mixture is then stirred at room temperaturefor another 1 h. 6 ml of water and 3 ml of 3 molar aqueous sodiumhydroxide solution are added to this mixture, and 2.3 ml of 35% strengthhydrogen peroxide are then metered in such that the internal temperatureremains between 30 and 50° C. The mixture is stirred at room temperaturefor another 1 h and then concentrated using a rotary evaporator, takenup in dichloromethane, washed twice with water and dried (magnesiumsulphate), and the solvent is distilled off. Chromatography on silicagel (ethyl acetate/hexane 1:4) gives 4.39 g (70%) of the desired product(I-a-1) as a viscous, colourless oil. The syn/anti-isomer ratioaccording to ¹H-NMR is about 85:15.

¹H-NMR (400 MHz, CDCl₃): δ=1.10 (mc, 6H), 3.02-3.15 (m, 1H), 3.40 (mc,1H), 3.55-3.69 (m, 2H), AB system: δ_(A)=4.78, δ_(B)=4.82, J=13 Hz(benzyl-CH ₂ anti-isosomer), 4.85 (s, benzyl-CH ₂ syn-isomer, 6.88 (mc,2H), 7.12 (mc, 2H), 7.30 (mc, 3H).

Example I-a-26-(Benzyloxy)-5-(2,6-diethyl-4-methylphenyl)-4-oxo-1,2,3,3a,4,6a-hexahydropentalene-2-carbaldehyde

At −78° C., 1.31 g (16.8 mmol) of dimethyl sulphoxide are slowly addeddropwise to 1.067 g (8.4 mmol) of oxalyl chloride in 40 ml ofdichloromethane, and the mixture is stirred at this temperature for 20min. 1.70 g (4.20 mmol) of3-(benzyloxy)-2-(2,6-diethyl-4-methylphenyl)-5-(hydroxymethyl)-4,5,6,6a-tetrahydropentalen-1(3aH)-one(Example I-a-1), dissolved in 30 ml of dichloromethane, are then slowlyadded dropwise, and the mixture is stirred for another hour. 2.13 g (21mmol) of triethylamine are then added slowly, and the mixture is broughtto room temperature. Addition of 50 ml of saturated ammonium chloridesolution, separation, washing of the organic phase with water, drying(magnesium sulphate), concentration on a rotary evaporator andchromatographic purification of the resulting crude product on silicagel (mobile phase ethyl acetate/hexane 1:5) gives 1.24 g (73%) of thetitle compound as a colourless oil.

¹H-NMR (400 MHz, CDCl₃): δ=1.08 and 1.12 (in each case t, in each case3H), 2.30 (s, 3H), 2.90 (mc, 1H), 3.12 (mc, 1H), 3.41 (mc, 1H), 4.72 (s,2H), 6.89 (mc, 2H), 9.70 (mc, 1H).

Example I-a-35-(2,6-Diethyl-4-methylphenyl)-4,6-dioxooctahydropentalene-2-carbaldehyde

20 mg of palladium on activated carbon (10%) are added to 1.10 g (2.72mmol) of6-(benzyloxy)-5-(2,6-diethyl-4-methylphenyl)-4-oxo-1,2,3,3a,4,6a-hexahydropentalene-2-carbaldehydein 20 ml of methanol, and the mixture is hydrogenated (15 bar, roomtemperature) for 20 h. The filtration and concentration on a rotaryevaporator give 0.82 g (97%) of the title compound (I-a-3, isomer ratioaccording to ¹H-NMR 4:1).

¹H-NMR (400 MHz, CDCl₃): δ=1.05 (mc, 6H), 2.90 (mc, 1H), 3.09-3.40 (m,br, 2H), 6.91 (mc, 2H), 9.62 (mc, CHO isomer 1), 9.68 (mc, CHO isomer2).

Example I-a-45-(2,6-Diethyl-4-methylphenyl)-4,6-dioxooctahydropentalene-2-carbonitrile

0.91 g (2.30 mmol) of2-(2,6-diethyl-4-methylphenyl)-5-formyl-3-oxooctahydropentalen-1-yl2,2-dimethylpropanoate (Example I-b-2), 0.78 g (11.48 mmol) of sodiumformate and 0.80 g (11.48 mmol) of hydroxylamine hydrochloride in 30 mlof formic acid are heated at reflux for 72 h. 50 ml of water are thenadded, and the mixture is stirred at room temperature for 1 h, taken upin ethyl acetate, washed twice with water, dried (magnesium sulphate)and concentrated using a rotary evaporator. The residue ischromatographed on silica gel (mobile phase ethyl acetate/hexane 1:6).This gives 0.31 g (44%) of the desired compound as a colourless oil.

¹H-NMR (400 MHz, CDCl₃): δ=1.08 and 1.11 (in each case t, in each case3H), 2.00 (mc, 2H), 2.48 (mc, 2H), 2.99 (mc, 1H), 6.95 (mc, 2H).

Example I-a-52-(2,6-Diethyl-4-methylphenyl)-5-(1,3-dioxan-2-yl)tetrahydropentalene-1,3(2H,3aH)-dione

0.100 g (0.22 mmol) of2-(2,6-diethyl-4-methylphenyl)-5-(1,3-dioxan-2-yl)-3-oxo-3,3a,4,5,6,6a-hexahydropentalen-1-yl2,2-dimethylpropanoate in 10 ml of methanol and 4 ml of 1N aqueoussodium hydroxide solution is stirred at room temperature for 2 h. Themixture is then concentrated, the residue is taken up in water, themixture is acidified to pH 4 using 2N HCl and extracted with ethylacetate, the extract is dried (magnesium sulphate) and the solvent isdistilled off. Chromatographic purification of the residue on silica gel(mobile phase ethyl acetate/hexane 1:6) gives 70 mg (86%) of the desiredcompound in the form of colourless needles of m.p. 100-101° C.

Example I-a-822-(2,6-diethyl-4-methylphenyl)-5-methoxymethyltetrahydropentalene-1,3-dione

0.762 g (1.88 mmol) of the compound I-a-1(3-(benzyloxy)-2-(2,6-diethyl-4-methylphenyl)-5-(hydroxymethyl)-4,5,6,6a-tetrahydropentalene-1(3aH)-one)in 5 ml of tetrahydrofuran is added dropwise to 93 mg (2.32 mmol) ofsodium hydride in 20 ml of tetrahydrofuran, and the mixture is stirredat room temperature for another 30 minutes. 309 mg (2.45 mmol) ofdimethyl sulphate, dissolved in 2 ml of tetrahydrofuran, are then slowlyadded dropwise, and the mixture is heated at reflux for 2 h. The mixtureis taken up in ethyl acetate, extracted twice with water, dried(magnesium sulphate), and the solvent is distilled off. Chromatographyon silica gel (mobile phase ethyl acetate/hexane 1:5) gives 0.50 g (64%)of the desired compound in the form of colourless crystals of m.p.75-76° C.

Example I-a-292-(2,6-diethyl-4-methylphenyl)-5-methoxymethyltetrahydropentalene-1,3-dione

After addition of 5 mg of catalyst (Pd/C, 5%), 80 mg (0.19 mmol) of thecompound I-a-82 in 10 ml of methanol are hydrogenated at roomtemperature and at a pressure of 5 bar. After filtration and removal ofthe solvent by distillation, 58 mg (92%) of the desired compound I-a-29are obtained as a yellowish oil.

¹H-NMR (400 MHz, CDCl₃): δ=1.08 and 1.11 (in each case t, in each case3H), 2.00 (mc, 2H), 2.48 (mc, 2H), 2.99 (mc, 1H), 6.95 (mc, 2H).

Example I-a-392-(2,6-diethyl-4-methylphenyl)-5-(3-oxobutyl)-tetrahydropentalene-1,3-dione

1.87 g (4.65 mmol) of6-(benzyloxy)-5-(2,6-diethyl-4-methylphenyl)-4-oxo-1,2,3,3a,4,6a-hexahydropentalene-2-carbaldehyde(compound I-a-2) and 1.63 g (5.11 mmol) ofacetonylidenetriphenylphosphorane in 40 ml of trichloromethane arestirred at room temperature for 12 h. The solvent is then removed, andthe residue is purified chromatographically on silica gel (mobile phaseethyl acetate/hexane 1:5). This gives 1.37 g (66%) of3-benzyloxy-2-(2,6-diethyl-4-methylphenyl)-5-(3-oxobut-1-enyl)-4,5,6,6a-tetrahydro-3aH-pentalen-1-oneas a colourless oil.

¹H-NMR (400 MHz, CDCl₃): δ=1.10 (mc, 6H), 2.25 (s, 3H), 2.31 (s, 3H),2.93, 3.19 and 3.44 (in each case mc, in each case 1H), 4.80 (s, H),6.12 (d, 1H), 6.74 (dd, 1H), 6.90 (mc, 2H)

20 mg of 5% Pd/C catalyst are added to 1.30 g (2.94 mmol) of thisintermediate in 40 ml of methanol, and the intermediate is hydrogenatedcatalytically at room temperature and a pressure of 5 bar for 10 h.Filtration and removal of the solvent by distillation give 1.040 g (99%)of the desired target compound I-a-39 in the form of yellowish crystalsof m.p. 60° C.

Example I-a-422-(2,6-diethyl-4-methylphenyl)-5-[3-methoxyiminobutyl]-tetrahydropentalene-1,3-dione

267 mg (0.82 mmol) of2-(2,6-diethyl-4-methylphenyl)-5-(oxobutyl)-tetrahydropentalene-1,3-dione(example I-a-39), 102 mg (1.23 mmol) of O-methylhydroxylaminehydrochloride and 0.5 ml of triethylamine in 10 ml of acetonitrile arestirred at room temperature overnight. The mixture is then taken up inethyl acetate, washed with water and dried (magnesium sulphate) and thesolvent is distilled off Chromatography on silica gel (mobile phaseethyl acetate/hexane 1:4) gives 225 mg (77%) of the target compound inthe form of colourless crystals of m.p. 79-80° C.

Example I-a-402-(2,6-diethyl-4-methylphenyl)-5-methoxymethoxymethyltetrahydropentalene-1,3-dione

200 mg (0.49 mmol) of the compound from example I-a-1, and 1.12 g (14.8mmol) of dimethoxyethane together with 10 mg of scandiumtrifluoromethanesulphonate are heated at reflux in 10 ml oftrichloromethane for 8 h. The reaction mixture is diluted with water,the phases are separated and the organic phase is washed with water and0.5 N aqueous sodium hydroxide solution, dried (magnesium sulphate) andconcentrated on a rotary evaporator. Chromatography on silica gel(mobile phase ethyl acetate/hexane 1:5) gives 130 mg (59%) of3-benzyloxy-2-(2,6-diethyl-4-methylphenyl)-5-methoxymethoxymethyl-4,5,6,6a-tetrahydro-3aH-pentalen-1-oneas a colourless oil.

¹H-NMR (400 MHz, CDCl₃): δ=1.10 (mc, 6H), 2.30 (s, 3H), 3.15 (mc, 1H),3.35 (s, 3H), 4.60 (s, 2H), 4.85 (s, 2 h), 6.89 (mc, 2H)

As described in example I-a-29, 123 mg (274 mmol) of this compound aresubjected to catalytical hydrogenation. This gives 95 mg (96%) of thetitle compound in the form of colourless crystals of m.p. 155-156° C.

Example I-a-772-(2,6-diethyl-4-methylphenyl)-5-{[(4,5-dimethyl-1,3-thiazol-2-yl)oxy]methyl}tetrahydropentalene-1,3(2H,3aH)-dione

0.83 g (2.05 mmol) of the compound I-a-1 and 0.123 g (3.07 mmol) ofsodium hydride in 30 ml of THF are heated at reflux for 30 minutes. 0.30g (2 mmol) of 2-chloro-4,5-dimethyl-1,3-thiazole is then added dropwiseat room temperature, and the mixture is heated at reflux for 2 h. Aftercooling, 5 ml of 2N hydrochloric acid are added carefully, and themixture is taken up in ethyl acetate, washed with water, dried(magnesium sulphate) and concentrated using a rotary evaporator.Chromatography on silica gel (mobile phase ethyl acetate/hexane 1:6)gives 0.31 g (30%) of3-benzyloxy-2-(2,6-diethyl-4-methylphenyl)-5-(4,5-dimethylthiazol-2-yloxymethyl)-4,5,6,6a-tetrahydro-3aH-pentalen-1-oneas a colourless oil.

¹H-NMR (400 MHz, CDCl₃): δ=1.10 (mc, 6H), 2.13, 2.20 and 2.32 (in eachcase s, in each case 3H), 3.15 and 3.40 (in each case mc, in each case1H), 4.25-4.35 (m, 2H), 4.82 (s, 2H), 4.60 (s, 2H), 6.90 and 7.12 (ineach case mc, in each case 2H), 7.30 (mc, 3H)

As described in example I-a-29, 0.170 g (0.33 mmol) of this compound issubjected to catalytical hydrogenation (methanol, 5% Pd/C, 5 bar). Thisgives 0.140 g (99%) of the desired title compound I-a-77 in the form ofcolourless crystals of m.p. 73-74° C.

¹H-NMR (400 MHz, CDCl₃): δ=1.05 (mc, 6H), 2.11, 2.19 and 2.31 (in eachcase s, in each case 3H), 2.62 (mc, 1H), 3.15-3.32 (m, 2H), 4.27 (d,2H), 6.91 (mc, 2H)

Example I-a-832-[5-(2,6-diethyl-4-methylphenyl)-4,6-dioxohexahydropentalen-2-ylidene]-malononitrile

0.500 g (1.70 mmol) of2-(2,6-diethyl-4-methylphenyl)tetrahydropentalene-1,3,5-trione (exampleI-a-4 from WO 2010/040460), 250 mg of malononitrile, 150 mg of ammoniumacetate and 0.3 ml of glacial acetic acid in 30 ml of toluene are heatedat reflux for 2 h. After cooling, the solvent is distilled off and themixture is taken up in ethyl acetate, washed twice with water, thendried (magnesium sulphate) and concentrated on a rotary evaporator. Whatremains is a yellow oil which is chromatographed on silica gel usingethyl acetate/hexane 1:6. This gives 0.32 g (56%) of a colourless oil.

¹H-NMR (400 MHz, CDCl₃): δ=1.02 and 1.08 (in each case t, in each case3H), 2.21 and 2.38 (in each case mc, in each case 2H), 2.31 (s, 3H),3.12 and 3.30 (in each case mc, in each case 2H), 3.40 and 3.58 (in eachcase mc, in each case 1H), 6.95 (mc, 2H).

Example I-a-352-[3aR,6aS)-5-(2,6-diethyl-4-methylphenyl)-4,6-dioxooctahydropentalen-2-yl]malononitrile

0.75 g (1.98 mmol) of sodium borohydride are added to 230 mg (0.66 mmol)of2-[5-(2,6-diethyl-4-methylphenyl)-4,6-dioxohexahydropentalen-2-ylidene]malononitrilein a mixture of 10 ml of methanol and 10 ml of tetrahydrofuran, and themixture is stirred at room temperature for 2 h. The solvent is distilledoff and the mixture is taken up in ethyl acetate, washed with water,dried (magnesium sulphate) and concentrated on a rotary evaporator.Chromatographic purification of the residue gives 140 mg (60%) of thedesired compound in the form of colourless crystals of m.p. 116-117° C.

¹H-NMR (400 MHz, CDCl₃): δ=1.06 (mc, 6H), 1.61 (mc, 2H), 2.31 (s, 3H),2.33 (mc, 4H), 2.50 (mc, 2H), 2.77 (mc, 1H), 3.82 (d, 1H), 6.95 (mc,2H).

Example I-a-84 Ethylcyano-[5-(2,6-diethyl-4-methylphenyl)-4,6-dioxohexahydropentalen-(2Z)-ylidene]acetate

3.37 g (11.29 mmol) of2-(2,6-diethyl-4-methylphenyl)tetrahydropentalene-1,3,5-trione, 2.55 g(22.59 mmol) of ethyl cyanoacetate, 870 mg (11.3 mmol) of ammoniumacetate and 2.5 ml of glacial acetic acid in 70 ml of toluene arereacted analogously to example I-a-82. This gives, after chromatographyon silica gel (ethyl acetate/hexane 1:6), 0.99 g (22%) of the desiredcompound as a colourless oil.

¹H-NMR (400 MHz, CDCl₃): δ=0.94 and 1.08 (in each case t, in each case3H), 1.32 (t, 3H), 2.20 (mc, 2H), 2.30 (s, 3H), 2.36 (mc, 2H), 3.10-3.20(mc, 2H), 4.28 (q, 2H), 6.90 (mc, 2H).

The following compounds of the formula (I-a) are obtained analogously toExamples (I-a-1) to (I-a-5) and in accordance with the generalstatements on the preparation:

(I-a)

Ex. No. R1 R2 R4 G Y—Q m.p. [° C.] or ¹H-NMR (400 MHz, CDCl₃, δ in ppm)Notes I-a-6  C₂H₅ CH₃ C₂H₅ H

δ = 1.07 and 1.20 (in each case mc, in each case 6H), 3.18 (mc, 2H),3.50 and 3.65 (in each case mc, in each case 2H), 4.27 and 4.31 (in eachcase d, Σ 1H), 6.92 (mc, 2H) syn/anti mixture I-a-7  C₂H₅ CH₃ C₂H₅ HHOCH₂— δ = 1.05-1.10 (m, 6H), 3.10-3.22 (m, 1H), 3.39 (mc, 1H),syn-isomer 3.55-3.68 (m, 2H, CH ₂OH), 6.94 (mc, 2H) I-a-8  C₂H₅ CH₃ C₂H₅H HO₂C— 124-125° C. anti-isomer I-a-9  C₂H₅ CH₃ C₂H₅ H CH₃O₂C— 72-73° C.anti-isomer I-a-10 C₂H₅ CH₃ C₂H₅ H

86-87° C. anti-isomer I-a-11 CH₃ CH₃ CH₃ H OHC— 131-132° C. syn/antimixture I-a-12 C₂H₅ CH₃ C₂H₅ H

71-72° C. anti-isomer I-a-13 C₂H₅ CH₃ C₂H₅ H CH₃O—N═CH— δ = 1.08 (t,6H), 2.93 (mc, 1H), 3.35 (mc, 2H), 3.71 (s, E/Z mixture 3H), 6.51 and7.30 (in each case d, Σ 1H) syn/anti mixture I-a-14 C₂H₅ CH₃ C₂H₅ HC₃H₅CH₂O—N═CH— δ = 0.25 and 0.52 (in each case mc, in each case 2H),2.95 E/Z mixture (mc, 1H), 3.10-3.42 (s, br, 2H), 3.50 (mc, 1H), 3.82and syn/anti 3.88 (in each case d, Σ 2H), 6.53 and 7.38 (in each case d,mixture Σ 1H) I-a-15 C₂H₅ CH₃ C₂H₅ H ^(i)PrO—N═CH— 68-69° C. E/Z mixturesyn/anti mixture I-a-16 C₂H₅ CH₃ C₂H₅ H

δ = 1.03 (mc, 6H), 3.05 and 3.33 (in each case mc, in each case 1H),4.10-4.18 and 4.33-4.39 (in each case m, in each case 2H), 4.52 and 4.59(in each case d, in each case 1H), 5.70 (s, 2H) syn/anti mixture I-a-17C₂H₅ CH₃ C₂H₅ H Cl₂C═CHCH₂O—N═CH— δ = 1.08 (t, 6H), 2.32 (s, 3H), 2.95(mc, 1H), 4.58 and 4.66 E/Z mixture (in each case d, Σ 2H), 6.10 (mc,1H), 6.60 and 7.37 (in syn/anti each case d, Σ 1H) mixture I-a-18 C₂H₅CH₃ C₂H₅ H HC≡CCH₂O—N═CH— 2.43 and 2.46 (in each case t, Σ 1H), 4.60 and4.65 (in E/Z mixture each case mc, Σ 2H), 6.62 and 7.38 (in each case d,Σ syn/anti 1H) mixture I-a-19 C₂H₅ CH₃ C₂H₅ H

δ = 0.70 and 1.15 (in each case s, in each case 3H), 1.08 (mc, 6H), 1.50and 2.20 (in each case mc, in each case 2H), 3.38 and 3.55 (in each cased, in each case 2H), 4.24 (d, 1H), anti-isomer I-a-20 C₂H₅ CH₃ C₂H₅ H

δ = 1.05 (mc, 6H), 1.15 (s, 9H), 2.02 and 3.30 (in each case mc, in eachcase 1H), 3.60 (mc, 3H), 4.08 (mc, 1H), 4.45 and 4.50 (in each case d, Σ1H), 6.92 (mc, 2H) syn/anti mixture I-a-21 C₂H₅ CH₃ C₂H₅ H HO—N═CH— δ =1.08 (mc, 6H), 2.32 (s, 3H), 3.20 and 3.41 (in each E/Z mixture case mc,in each case 1H), 6.64 and 7.40 (in each case d, syn/anti Σ 1H), 6.95(mc, 2H) mixture I-a-22 C₂H₅ CH₃ C₂H₅ H CH₃O δ = 1.05-1.10 (m, 6H), 2.30(s, 3H), 3.05-3.30 (s, broad, syn-isomer 2H), 3.18 (s, 3H), 3.87 (mc,1H). I-a-23 C₂H₅ CH₃ C₂H₅ H OH 114-115° C. syn-isomer I-a-24 C₂H₅ CH₃C₂H₅ H

127-128° C. syn/anti mixture I-a-25 C₂H₅ CH₃ C₂H₅ H

δ = 1.05 (t, 6H), 2.32 (s, 3H), 3.59 (mc, 1H), 4.14 (mc, 1H), 4.66 and4.70 (in each case d, Σ 1H), 6.91 (s, 2H) syn/anti mixture I-a-26 C₂H₅CH₃ C₂H₅ H

103-104° C. syn/anti mixture I-a-27 CH₃ CH₃ CH₃ H CH₃O—N═CH— 204-205° C.E/Z mixture syn/anti mixture I-a-28 C₂H₅ CH₃ C₂H₅ H CH₃(C═O)OCH₂—101-103° C. syn-isomer I-a-29 C₂H₅ CH₃ C₂H₅ H CH₃OCH₂— 159-160° C.syn-isomer I-a-30 CH₃ CH₃ CH₃ H

97-98° C. syn/anti mixture I-a-31 CH₃ CH₃ CH₃ H iPrO—N═CH— δ = 1.18 and1.20 (in each case d, in each case 3H), 2.05 E/Z mixture (s, 6H), 2.28(s, 3H), 4.25 (mc, 1H), 6.51 and 7.30 (in syn/anti each case d, Σ 1H),6.88 (mc, 2H) mixture I-a-32 CH₃ CH₃ CH₃ H

135-136° C. syn/anti mixture I-a-33 C₂H₅ CH₃ C₂H₅ H CH₃C═O— 90-91° C.syn/anti mixture I-a-34 C₂H₅ CH₃ C₂H₅ H CH₃C(═NOCH₃)— 195-196° C. E/Zmixture syn/anti mixture I-a-35 C₂H₅ CH₃ C₂H₅ H (NC)₂CH— 116-117° C.syn/anti mixture I-a-36 C₂H₅ CH₃ C₂H₅ H —CH₂CH₂CO₂CH₃ 59-60° C. syn/antimixture I-a-37 C₂H₅ CH₃ C₂H₅ H —CH₂CH₂CN 142-145° C. syn/anti mixtureI-a-38 C₂H₅ CH₃ C₂H₅ H

142-145° C. syn/anti mixture I-a-39 C₂H₅ CH₃ C₂H₅ H CH₃(C═O)CH₂CH₂— δ =1.08 (mc, 6H), 2.12 (s, 3H), 2.30 (s, 3H), 3.28 (mc, syn/anti 2H), 6.92(mc, 2H) mixture I-a-40 C₂H₅ CH₃ C₂H₅ H CH₂OCH₂OCH₂— δ = 1.08 (mc, 6H),2.31 (s, 3H), 3.23 (mc, 2H), 3.34 (s, syn/anti 3H), 3.50 (d, 2H), 4.60(s, 2H), 6.92 (mc, 2H) mixture I-a-41 C₂H₅ CH₃ C₂H₅ H CH₃CH(OH)— 71-72°C. syn/anti mixture racemate I-a-42 C₂H₅ CH₃ C₂H₅ H CH₃C(═NOCH₃)CH₂—CH₂—79-80° C. E/Z mixture syn/anti mixture I-a-43 C₂H₅ CH₃ C₂H₅ H C₂H₅OCH₂—δ = 1.08 (t, 6H), 1.19 (t, 3H), 3.15 (mc, 1H), 3.47 (mc, syn/anti 3H),3.48 (q, 2H), 6.92 (mc, 2H) mixture I-a-44 C₂H₅ CH₃ C₂H₅ HC₆H₅NH(C═O)OCH₂— 101-102° C. syn/anti mixture I-a-45 C₂H₅ CH₃ C₂H₅ HC₂H₅O₂C— δ = 1.08 (mc, 6H), 1.25 (mc, 3H), 1.88 and 2.00 (in eachsyn/anti case mc, Σ 2H), 2.99 (mc, 1H), 4.12 (q, 2H), 6.90 (mc, mixture2H) I-a-46 C₂H₅ CH₃ C₂H₅ H CH₃(C═O)SCH₂— δ = 1.08 (t, 6H), 2.30 (s, 3H),2.34 (s, 3H), 2.95, (d, 2H), syn/anti 3.22 (mc, 2H), 6.91 (mc, 2H)mixture I-a-47 C₂H₅ CH₃ C₂H₅ H C₆H₅CH₂NH(C═O)—OCH₂— 101-102° C. syn/antimixture I-a-48 C₂H₅ CH₃ C₂H₅ H CH₃SO₂CH₂— 180-181° C. syn/anti mixtureI-a-49 C₂H₅ CH₃ C₂H₅ H NCCH₂— 66-67° C. syn/anti mixture I-a-50 C₂H₅ CH₃C₂H₅ H H₂N(C═O)— 161-162° C. syn/anti mixture I-a-51 C₂H₅ CH₃ C₂H₅ HH₂N(C═O)OCH₂— 90-91° C. syn/anti mixture I-a-52 C₂H₅ CH₃ C₂H₅ H(CH₃)₂N(C═O)OCH₂— 151-152° C. syn/anti mixture I-a-53 C₂H₅ CH₃ C₂H₅ HCH₃NH(C═O)— δ = 1.10 (mc, 6H), 2.32 (s, 3H), 2.82 (mc, 1H), 3.49 (d,syn/anti 3H), 6.95 (mc, 2H) mixture I-a-54 C₂H₅ CH₃ C₂H₅ H

131-132° C. syn/anti mixture I-a-55 C₂H₅ CH₃ C₂H₅ H (CH₃)₂N(C═O)—131-132° C. syn/anti mixture I-a-56 C₂H₅ CH₃ C₂H₅ benzyl —CHO δ = 1.08and 1.12 (in each case t, in each case 3H), 2.72 syn/anti and 2.90 (ineach case mc, Σ 1H), 3.11 and 3.91 (in each mixture case mc, in eachcase 1H), 4.71 and 4.77 (s and mc, Σ 1H), 6.90 (mc, 2H), 7.10-7.35 (m,5H) I-a-57 C₂H₅ CH₃ C₂H₅ benzyl CH₃C═O— δ = 1.09 and 1.12 (in each caset, in each case 3H), 1.90 syn/anti and 2.03 (in each case mc, in eachcase 1H), 2.80, 3.08 mixture and 3.41 (in each case mc, in each case1H), 4.78 and 4.80 (AB system, J = 12 Hz, 2H), I-a-58 C₂H₅ CH₃ C₂H₅benzyl CH₃O₂CCH═CH— 90-91° C. syn/anti mixture E/Z mixture I-a-59 C₂H₅CH₃ C₂H₅ benzyl —CH═CHCN δ = 1.10 (mc, 6H), 3.10-3.50 (m, 3H), 4.75-4.85(m, 2H), syn/anti 5.30 and 5.33, (in each case d, Σ 1H), 6.88 and 6.70(in mixture each case d, Σ 1H), 6.90 (mc, 2H) E/Z mixture I-a-60 C₂H₅CH₃ C₂H₅ H CH₃SCH₂— δ = 1.08 (t, 6H), 2.10 (s, 3H), 2.29 (s, 3H),2.20-2.42 (m, syn/anti 4H), 3.25 (mc, 2H), 6.90 (mc, 2H) mixture I-a-61C₂H₅ CH₃ C₂H₅ benzyl BrCH₂— δ = 1.09 (mc, 6H), 1.51-1.70 (m, 2H), 3.02(mc, 1H), 3.40 syn/anti (mc, 2H), 3.48 (mc, 1H), 4.79 (mc, 2H), mixture6.90 (mc, 2H) I-a-62 C₂H₅ CH₃ C₂H₅ benzyl H₂N(C═O)OCH₂— δ = 1.09 (mc,6H), 1.38-1.65 (m, 2H), 3.12 and 3.40 (in syn/anti each case mc, in eachcase 1H), 4.05 (mc, 2H), 4.60 (s, mixture br), 4.80 and 4.82 (in eachcase mc, Σ 2H), 6.90 (mc, 2H), 7.10-7.35 (m, 5H) I-a-63 C₂H₅ CH₃ C₂H₅benzyl C₆H₅NH(C═O)OCH₂— 60-61° C. syn/anti mixture I-a-64 C₂H₅ CH₃ C₂H₅benzyl CF₃(C═O)OCH₂— δ = 1.09 (mc, 6H), 1.38-1.62 (m, 2H), 2.33 (s, 3H),3.10- syn/anti 3.70 (m, 3H), 4.80-4.91 (m, 2H), 6.90 (mc, 2H), 7.12-7.35mixture (m, 5H) I-a-65 C₂H₅ CH₃ C₂H₅ benzyl (CH₃)₂N(C═O)— 111-112° C.syn/anti mixture I-a-66 C₂H₅ CH₃ C₂H₅ H (CH₃)₃C(C═O)SCH₂— δ = 1.08 (mc,6H), 1.21 (s, 9H), 2.30 (s, 3H), 2.92 (d, 2H), syn/anti 3.12 and 3.35(in each case mc, in each case 1H), 6.93 mixture (mc, 2H), I-a-67 C₂H₅CH₃ C₂H₅ H CF₃(C═O)OCH₂— 214-215° C. syn/anti mixture I-a-68 C₂H₅ CH₃C₂H₅ H CF₃CH(OH)— 185-186° C. syn/anti mixture I-a-69 C₂H₅ CH₃ C₂H₅benzyl CH₂═CH— δ = 1.11 (mc, 6H), 1.40-1.69 (m, 2H), 3.00-3.15 (m, 1H),syn/anti 3.38 (mc, 1H), 4.75-4.85 (m, 2H), 4.95-5.10 (m, 2H), 5.80mixture (mc, 1H), 6.90 (mc, 2H), 7.12-7.33 (m, 5H) I-a-70 C₂H₅ CH₃ C₂H₅H BrCH₂— δ = 1.09 (mc, 6H), 1.40-1.55 (m, 2H), 2.30 (s, 3H), 2.60syn/anti (mc, 1H), 3.25 (mc, 1H), 3.48 (mc, 2H), 3.71 (mc, 1H), mixture6.90 (mc, 2H) I-a-71 C₂H₅ CH₃ C₂H₅ H CH₂═CHCH₂—SCH₂— δ = 1.07 (mc, 6H),2.31 (s, 3H), 3.12 (d, 2H), 3.15-3.35 syn/anti (m, 2H), 5.05-5.15 (mc,2H), 5.55-5.62 (m, 1H), 6.90 (mc, mixture 2H) I-a-72 C₂H₅ CH₃ C₂H₅ H(CH₃)₂CHCH₂—SCH₂— δ = 0.99 (mc, 6H), 1.07 (mc, 6H), 1.79 (hept, 1H),2.40 (d, syn/anti 2H), 2.55 (mc, 2H), 3.15-3.35 (m, 2H), 6.90 (mc, 2H)mixture I-a-73 C₂H₅ CH₃ C₂H₅ H

δ = 1.06 (mc, 6H), 1.31-1.55 (m, 2H), 2.30 (s, 3H), 2.55 (mc, 1H),3.15-3.55 (m, 3H), 6.90 (d, 1H), 6.92 (mc, 2H), 7.10 (d, 1H) syn/antimixture I-a-74 C₂H₅ CH₃ C₂H₅ H (CH₃)₂CHCH₂—SO₂CH₂— δ = 1.07 (mc, 6H),1.12 (d, 6H), 2.75 (mc, 1H), 2.88 (d, syn/anti 2H), 3.00 (mc, 1H), 3.15(mc, 1H), 3.38 (mc, 1H), 6.92 mixture (mc, 2H) I-a-75 C₂H₅ CH₃ C₂H₅benzyl CF₃CH(OH)— 87-88° C. syn/anti mixture I-a-76 C₂H₅ CH₃ C₂H₅ H

δ = 1.05 (mc, 6H), 2.50-2.85 (m, Σ 1H), 3.15-3.41 (m, 2H), 4.51, d, 2H),6.93 (mc, 2H), 7.15-7.45 (m, 4H) syn/anti mixture I-a-77 C₂H₅ CH₃ C₂H₅ H

73-74° C. syn/anti mixture I-a-78 C₂H₅ CH₃ C₂H₅ H NCSCH₂— 87-88° C.syn/anti mixture I-a-79 C₂H₅ CH₃ C₂H₅ H

74-75° C. syn/anti mixture I-a-80 C₂H₅ CH₃ C₂H₅ H

δ = 1.05 (mc, 6H), 1.88 (mc, 2H), 2.05 (mc, 1H), 2.60- 2.71 (m, 4H),3.05-3.36 (m, 2H), 3.60-4.00 (m, 4H), 6.93 (mc, 2H) syn/anti mixtureI-a-81 C₂H₅ CH₃ C₂H₅ C₂H₅ —CH₂CO₂C₂H₅ δ = 1.05 (mc, 6H), 1.22 (t, 3H),2.51 (mc, 1H), 3.20 (mc, syn/anti 2H), 4.12 (q, 2H), 6.91 (mc, 2H)mixture I-a-82 C₂H₅ CH₃ C₂H₅ benzyl CH₂OCH₂—

Example I-b-12-(2,6-Diethyl-4-methylphenyl)-5-(methoxyimino)methyl-3-oxo-3,3a,4,5,6,6a-hexahydropentalen-1-yl2,2-dimethylpropanoate

0.104 g (0.31 mmol) of5-(2,6-diethyl-4-methylphenyl)-6-hydroxy-4-oxo-1,2,3,3a,4,6a-hexahydropentalene-2-carbaldehydeO-methyloxime (compound I-a-13 according to the invention), 0.040 g(0.34 mmol) of pivaloyl chloride and 92 mg (0.91 mmol) of triethylaminein 8 ml of dichloromethane are stirred at room temperature for 2 h. Themixture is poured onto ice, taken up in dichloromethane, washed withwater, dried (magnesium sulphate) and concentrated using a rotaryevaporator. Chromatography on silica gel (mobile phase ethylacetate/hexane v:v=25:75) gives 107 mg of the title compound as acolourless oil.

¹H-NMR (400 MHz, CDCl₃): δ=1.04 and 1.09 (in each case t, in each case3H), 1.08 (s, 9H), 2.98 (mc, 3H), 3.30 (mc, 1H), 3.80 (s, 3H), 4.00 (mc,1H), 6.88 (s, 1H), 7.31 (d, J=7 Hz, —CH═NOCH₃).

The following compounds of the formula (I-b) are obtained analogously toExample (I-b-1) and in accordance with the general statements on thepreparation:

(I-b)

Ex. No. R¹ R² R⁴ R¹⁹ Y—Q m.p. [° C.] or ¹H-NMR (400 MHz, CDCl₃, δ inppm) Notes I-b-2  C₂H₅ CH₃ C₂H₅ tBu —CHO δ = 1.10 (s, 9H), 2.98, 3.37and 4.04 (in each case mc, in syn/anti mixture each case 1H), 9.66 (d,1H, CHO) I-b-3  C₂H₅ CH₃ C₂H₅ tBu

127° C. syn/anti mixture I-b-4  C₂H₅ CH₃ C₂H₅ tBu

δ = 1.05 (s, 9H), 1.42-1.58 (m, 3H), 3.22 (mc, 1H), 3.81- 3.98 (m, 5H),4.75 (d, 1H) syn/anti mixture I-b-5  C₂H₅ CH₃ C₂H₅ tBu

δ = 1.05 (s, 9H), 1.33-1.50 (m, 2H), 3.34 and 3.35 (in each case s, Σ3H), 3.95 (mc, 1H), 4.18 (d, 1H), 6.86 (s, 2H) syn/anti mixture I-b-6 C₂H₅ CH₃ C₂H₅ tBu C₃H₅CH₂O—N═CH— δ = 0.25 and 0.52 (in each case mc, ineach case 2H), E/Z mixture 1.08 (s, 9H), 3.28 (mc, 1H), 3.82 and 3.89(in each case syn/anti mixture d, Σ2H, CH ₂C₃H₅), 4.00 (mc, 1H), 6.59and 7.38 (in each case d, Σ2H, CH═NO) I-b-7  C₂H₅ CH₃ C₂H₅ tBuCl₂C═CHCH₂O—N═CH— δ = 1.04 (s, 9H), 2.30 (s, 3H), 3.28 and 4.02 (in eachE/Z mixture case mc, in each case 1H), 4.60 and 4.67 (in each case d,syn/anti mixture Σ 2H), 6.10 (mc, 1H), 6.88 (s, 2H) I-b-8  C₂H₅ CH₃ C₂H₅tBu CH₂═CHCH₂O—N═CH— δ = 1.05 (s, 9H), 3.28 and 4.00 (in each case mc,in each E/Z mixture case 1H), 4.50-4.61 (m, 2H), 5.18-5.32 (m, 2H), 5.96syn/anti mixture (mc, 1H), 6.51 and 7.39 (in each case d, Σ 1H) I-b-9 C₂H₅ CH₃ C₂H₅ tBu HC≡CCH₂O—N═CH— δ = 1.00-1.11 (m, 15H), 2.45 (mc, 1H),3.00 and 3.52 (in E/Z mixture each case mc, Σ 1H), 3.28 and 4.00 (ineach case mc, in syn/anti mixture each case 1H), 4.60 and 4.67 (in eachcase d, Σ 2H), 6.70 and 7.40 (in each case d, Σ 1H) I-b-10 C₂H₅ CH₃ C₂H₅iPr

δ = 1.00-1.11 (m, 12H), 2.56 (hept, 1H), 3.15 and 3.92 (in each case mc,in each case 1H), 4.18 and 4.40 (in each case mc, in each case 2H), 4.55and 4.58 (in each case d, Σ 1H) syn/anti mixture I-b-11 C₂H₅ CH₃ C₂H₅tBu

δ = 1.00 (t, 6H), 1.15 (s, 9H), 2.28 (s, 3H), 3.61 and 4.09 (in eachcase s, in each case 2H), 4.48 and 4.51 (in each case d, Σ 1H) syn/antimixture I-b-12 C₂H₅ CH₃ C₂H₅ tBu

99-100° C. syn/anti mixture I-b-13 C₂H₅ CH₃ C₂H₅ iPr CH₃O—N═CH— δ =1.00-1.12 (m, 12H), 2.31 (s, 3H), 3.81 and 3.87 (in E/Z mixture eachcase s, Σ 1H), 4.00 (mc, 1H), 6.59 and 7.32 (in each syn/anti mixturecase s, Σ 1H), I-b-14 C₂H₅ CH₃ C₂H₅ C₂H₅ CH₃O—N═CH— δ = 1.02-1.11 (m,9H), 2.33 (s, 3H), 3.18-3.30 (m, 1H), E/Z mixture 3.80 and 3.86 (in eachcase s, Σ 1H), 3.98-4.08 (m, 1H), syn/anti mixture 6.59 and 7.31 (ineach case s, Σ 1H), 6.90 (s, 2H) I-b-15 C₂H₅ CH₃ C₂H₅ iPr

δ = 0.70 and 1.12 (in each case s, in each case 3H), 1.02 and 1.08 ineach case mc, in each case 6H), 2.57 (hept, 1H), 3.40 and 3.58 (in eachcase mc, in each case 2H), 4.30 and 4.35 (in each case d, Σ 1H), 6.89(mc, 2H) syn/anti mixture I-b-16 C₂H₅ CH₃ C₂H₅ iPr

δ = 1.02 and 1.08 (in each case mc, in each case 6H), 2.58 (hept, 1H),3.33 (mc, 6H), 4.18 and 4.20 (in each case d, Σ 1H), 6.99 (s, 2H)syn/anti mixture I-b-17 C₂H₅ CH₃ C₂H₅ C₂H₅

δ = 1.03-1.12 (m, 9H), 2.31 (s, 3H), 2.52 (mc, 1H), 3.30- 3.35 (m, 6H),3.92-4.04 (m, 1H), 4.19 (mc, 1H), 6.90 (m, 2H) syn/anti mixture I-b-18C₂H₅ CH₃ C₂H₅ tBu

δ = 1.00 (t, 6H), 1.21 (s, 9H), 2.28 (s, 3H), 3.21 and 3.92 (in eachcase mc, in each case 1H), 4.03 and 4.09 (in each case d, Σ 1H), 6.85(mc, 2H) syn/anti mixture I-b-19 C₂H₅ CH₃ C₂H₅ tBu

δ = 1.00 and 1.08 (in each case t, Σ 6H), 1.09 (s, 9H), 1.91 (mc, 2H),3.05-3.19 (m, 1H), 3.35-4.47 (m, 1H), 4.12 (mc, 2H) syn/anti mixtureI-b-20 C₂H₅ CH₃ C₂H₅ iPr

133-134° C. syn/anti mixture I-b-21 C₂H₅ CH₃ C₂H₅ iPr

δ = 1.00-1.11 (m, 9H), 2.52 (hept, 1H), 3.15-3-25 (m, 5H), 3.90-4.01 (m,1H), 4.48 and 4.50 (in each case d, Σ1H), 6.87 (s, 2H) syn/anti mixtureI-b-22 C₂H₅ CH₃ C₂H₅ tBu

δ = 1.03 (t, 6H), 1.06 (s, 9H), 3.15-3.26 (m, 5H), 3.90- 4.00 (m, 1H),4.48-4.51 (m, 1H), 6.86 (s, 2H) syn/anti mixture I-b-23 C₂H₅ CH₃ C₂H₅iPr CH₃(C═O)OCH₂— δ = 1.03 (mc, 6H), 1.10 (mc, 6H), 2.05 (s, 3H), 2.30(s, syn/anti mixture 3H), 3.15-3.29 (m, 1H), 3.93-4.10 (m, 3H), 6.89 (s,2H) I-b-24 C₂H₅ CH₃ C₂H₅ tBu BrCH₂— 106-107° C. syn/anti mixture I-b-25C₂H₅ CH₃ C₂H₅ tBu

δ = 1.04 (mc, 6H), 1.07 (s, 9H), 1.30 (t, 3H), 3.12 (mc, 1H), 3.21 (d,2H), 3.30 (mc, 1H), 4.03 (mc, 1H), 4.23 (q, 2H), 6.88 (mc, 2H) syn/antimixture I-a-26 C₂H₅ CH₃ C₂H₅ iPr C₆H₅NH(C═O)OCH₂— δ = 1.00-1.11 (mc,12H), 1.30-1.62 (m, 2H), 2.59 (mc, syn/anti mixture 2H), 3.26 (mc, 1H),3.95-4.04 (m, 1H), 4.16 (d, 2H), 6.89 (mc, 2H), 7.08 (mc, 1H), 7.25-7.40(m, 4H) I-b-27 C₂H₅ CH₃ C₂H₅ iPr C₆H₅CH₂NH(C═O)OCH₂— δ = 1.01-1.11 (mc,12H), 1.22-1.60 (m, 2H), 2.48-2.60 syn/anti mixture (m, 2H), 3.15-3.29(m, 1H), 3.90-4.04 (m, 1H), 4.11 (d, 2H), 4.38 (mc, 2H), 6.89 (mc, 2H),7.08 (mc, 1H), 7.25- 7.40 (m, 4H) I-b-28 C₂H₅ CH₃ C₂H₅ tBu

δ = 1.05 (mc, 6H), 1.07 (s, 9H), 2.28 (s, 3H), 2.61 (mc, 1H), 3.20-3.33(m, 3H), 6.89 (mc, 2H), 7.25-7.38 (m, 5H) syn/anti mixture

Example I-c-12-(2,6-Diethyl-4-methylphenyl)-5-(dimethoxymethyl)-3-oxo-3,3a,4,5,6,6a-hexahydropentalen-1-ylethyl carbonate

At room temperature, 80 mg (0.80 mmol) of trimethylamine are addeddropwise to 0.090 g (0.25 mmol) of2-(2,6-diethyl-4-methylphenyl)-5-(dimethoxymethyl)-3-hydroxy-4,5,6,6a-tetrahydropentalen-1(3aH)-one(compound I-a-9 according to the invention) and 30 mg (0.28 mmol) ofethyl chloroformate in 15 ml of dichloromethane, and the mixture isstirred for another 1 h. The mixture is poured onto ice-water, taken upin dichloromethane, washed with water, dried (magnesium sulphate), andthe solvent is distilled off.

Chromatographic purification on silica gel (ethyl acetate/hexane=1:4)gives 88 mg (81%) of the desired compound in the form of colourlesscrystals of melting point 95-96° C.

¹H-NMR (400 MHz, CDCl₃): δ=1.06, 1.10 and 1.25 (in each case t, in eachcase 3H), 1.40-1.50 (m, 2H), 2.18 (mc, 1H), 2.53 (mc, 1H), 3.21 (mc,1H), 3.32 (s, 6H), 4.02 (mc, 1H), 4.18 (q, 2H), 6.90 (mc, 1H) ppm

The following compounds of the formula (I-c) are obtained analogously toExamples (I-c-1) according to the general statements on the preparation:

(I-c)

Ex. No. R¹ R² R⁴ R²⁰ Y—Q m.p. [° C.] or ¹H-NMR (400 MHz, CDCl₃, δ inppm) Notes I-c-2  C₂H₅ CH₃ C₂H₅ C₂H₅

δ = 1.05 (mc, 6H), 1.24 (t, 3H), 3.15 and 3.24 (mc, 1H), 4.00 (mc, 1H),4.18 (mc, 4H), 4.33-4.43 (m, 2H), 4.55 and 4.58 (in each case d, Σ 1H),5.70 (s. 2H), 6.90 (s, 2H) syn/anti mixture I-c-3  C₂H₅ CH₃ C₂H₅ C₂H₅

δ = 1.07 (mc, 6H), 1.25 (t, 3H), 3.61 and 3.88 (in each case mc, in eachcase 2H), 4.00 (mc, 1H), 4.19 (mc, 2H) 4.48 and 4.51 (in each case d, Σ1H), 6.90 (s, 2H) syn/anti mixture I-c-4  C₂H₅ CH₃ C₂H₅ C₂H₅

δ = 0.70 (s, 3H), 1.08 (mc, 6H), 1.12 (s, 3H), 1.24 (t, 3H), 3.22 (mc,1H), 3.40 and 3.58 (in each case d, in each case 2H), 4.18 (mc, 2H),4-30 (d, 1H), 6.90 (mc, 2H) syn/anti mixture I-c-5  C₂H₅ CH₃ C₂H₅ C₂H₅^(i)PrO—N═CH— δ = 1.05-1.12 (m, 3H), 1.18-1.28 (m, 6H), 3.00 (mc, E/Zmixture 1H), 4.00-4.32 (m. 4H), 6.58 and 7.31 (in each case d, syn/antimixture Σ 1H), I-c-6  C₂H₅ CH₃ C₂H₅ C₂H₅ Cl₂C═CHCH₂O—N═CH— δ = 1.10 (mc,6H), 1.25 (mc, 3H), 3.00 (mc, 1H), 4.05 E/Z mixture (mc, 1H), 4.20 (mc,2H), 4.60 and 4.66 (in each case d, syn/anti mixture Σ 2H), 6.10 (mc,1H), 6.63 and 7.45 (in each case d, Σ 1H) I-c-7  C₂H₅ CH₃ C₂H₅ C₂H₅C₃H₅CH₂O—N═CH— δ = 0.25 and 0.53 (in each case mc, in each case 2H), E/Zmixture 1.10 (mc, 6H), 1.24 (mc, 3H), 3.28 (mc, 1H), 3.33 and syn/antimixture 3.39 (in each case d, Σ 2H), 4.19 (mc, 2H), 6.60 and 7.38 (ineach case d, Σ 1H), 6.90 (mc, 2H) I-c-8  C₂H₅ CH₃ C₂H₅ C₂H₅CH₂═CHCH₂O—N═CH— δ = 1.10 (mc, 6H), 1.21 (mc, 3H), 4.05 (mc, 1H), 4.20E/Z mixture (mc, 2H), 4.50 and 4.50 (in each case d, Σ 1H), 5.90-syn/anti mixture 6.02 (m, 1H), 6.61 and 7.48 (in each case d, Σ 1H)I-c-9  C₂H₅ CH₃ C₂H₅ CH₃

δ = 1.05-1.10 (m, 6H), 2.31 (s, 3H), 3.15-3.28 (m, 1H), 3.35 (mc, 6H),3.79 (s, 3H), 4.03 (mc, 1H), 4.18 and 4.20 (in each case d, Σ 1H)syn/anti mixture I-c-10 C₂H₅ CH₃ C₂H₅ iPr

δ = 1.05-1.12 (m, 6H), 1.21-1.27 (m, 6H), 3.30-3.35 (m, 6H), 4.02 (mc,1H), 4.18 and 4.21 (in each case d, Σ 1H), 4.82 (hept, 1H), 6.90 (mc,2H) syn/anti mixture I-c-11 C₂H₅ CH₃ C₂H₅ C₂H₅

δ = 1.25 (mc, 3H), 2.80-2.92 (m, 4H), 3.12-3.26 (m, 1H), 3.97-4.21 (m,4H), 6.90 (s, 2H) syn/anti mixture I-c-12 C₂H₅ CH₃ C₂H₅ C₂H₅

δ = 1.08 (mc, 6H), 1.24 (mc, 3H), 2.75, 3.01, 3.58 (in each case mc, ineach case 1H), 4.10-4.22 (m, 3H), 4.69 (mc, 1H), 6.89 (s, 2H) syn/antimixture I-c-13 C₂H₅ CH₃ C₂H₅ C₂H₅

δ = 1.24 (mc, 3H), 3.25 (mc, 5H), 4.00 (mc, 1H), 4.18 (mc, 2H), 4.48 and4.50 (in each case d, Σ 1H), 6.90 (mc, 2H) syn/anti mixture I-c-14 C₂H₅CH₃ C₂H₅ iPr CH₃O—N═CH— δ = 1.09 (mc, 6H), 1.23 (mc, 6H), 1.48-1.64 (m,2H), E/Z mixture 3.28 (mc, 1H), 3.81 and 3.82 (in each case s, Σ 3H),syn/anti mixture 4.05 (mc, 1H), 4.81 (mc, 1H), 6.60 and 7.31 (in eachcase d, Σ 1H), 6.90 (mc, 2H) I-c-15 C₂H₅ CH₃ C₂H₅ C₂H₅ CH₃(C═O)OCH₂— δ =1.08 (mc, 6H), 1.25 (mc, 3H), 1.31-1.45 (m, 2H), syn/anti mixture 2.05and 2.06 (in each case s, Σ 3H), 2.30 (s, 3H), 3.18-3.30 (m, 1H), 4.03(mc, 3H), 4.20 (mc, 1H), 6.9 (mc, 2H) I-c-16 C₂H₅ CH₃ C₂H₅ C₂H₅—CH₂CO₂C₂H₅ δ = 1.08 (mc, 6H), 1.22-1.35 (m, 6H), 2.28-2.45 (m, syn/antimixture 8H), 2.30 (s, 3H), 2.85 (mc, 1H), 3.26 (mc, 1H), 4.03 (q, 1H),4.14 (q, 2H), 4.18 (mc, 1H), 6.91 (mc, 2H) I-c-17 C₂H₅ CH₃ C₂H₅ C₂H₅CH₃C═O— δ = 1.06 (mc, 6H), 1.23 (mc, 3H), 2.00 (mc, 2H), 2.20 syn/antimixture (s, 3H), 2.31 (s, 3H), 2.82 (mc, 1H), 3.22 (mc, 1H), 4.03 (mc,1H), 4.18 (mc, 1H), 6.92 (mc, 2H) I-c-18 C₂H₅ CH₃ C₂H₅ C₂H₅CH₃C(═NOCH₃)— δ = 1.09 (mc, 6H), 1.25 (t, 3H), 1.81 (s, 3H) 1.93 (mc,E/Z mixture 2H), 2.09 (mc, 1H), 2.59 (mc, 1H), 3.20 (mc, 1H), 3.81syn/anti mixture (s, 3H), 1.71 (mc, 2H), 2.31 (s, 3H), 3.20 (mc, 1H),3.81 (s, 3H), 4.03 (mc, 1H), 4.18 (mc, 2H) I-c-19 C₂H₅ CH₃ C₂H₅ C₂H₅—CH₂CH₂CO₂CH₃ δ = 1.08 (mc, 6H), 1.23 (mc, 3H), 1.71 (mc, 2H), 2.31syn/anti mixture (s, 3H), 3.12-3.25 (m, 1H), 3.66 and 3.67 (in each cases, Σ 3H), 3.97 (mc, 1H), 4.19 (mc, 2H), 6.90 (mc, 2H) I-c-20 C₂H₅ CH₃C₂H₅ iPr —CH₂CH₂CO₂CH₃ δ = 1.07 (mc, 6H), 1.09 (mc, 3H), 1.70 (mc, 2H),2.31 syn/anti mixture (s, 3H), 2.57 (hept, 1H), 3.10-3.25 (m, 1H), 3.67and 3.68 (in each case s, Σ 3H), 3.88-3.95 (m, 1H), 6.90 (mc, 2H) I-c-21C₂H₅ CH₃ C₂H₅ C₂H₅ —CH₂CH₂CN δ = 1.08 (mc, 6H), 1.22 (mc, 3H), 2.33,1.78 (mc, 2H), syn/anti mixture (s, 3H), 3.12-3.30 (m, 1H), 4.00 (mc,1H), 4.18 (mc, 2H), 6.88 (mc, 2H) I-c-22 C₂H₅ CH₃ C₂H₅ C₂H₅ —CH═CHCN δ =1.08 (mc, 6H), 1.24 (mc, 3H), 1.65-1.80 (m, 2H), syn/anti mixture 2.31(s, 3H), 3.20-3.29 (m, 1H), 4.05 (mc, 1H), 4.18 E-isomer (mc, 2H), 5.45(J = 13 Hz, 1H), 6.77 (dd, J = 13 and 5 Hz, 1H), 6.90 (mc, 2H) I-c-23C₂H₅ CH₃ C₂H₅ C₂H₅ CH₃(C═O)CH₂CH₂— δ = 1.08 (mc, 6H), 1.25 (mc, 3H),2.23 and 2.24 (in syn/anti mixture each case s, Σ 3H), 2.31 (s, 3H),3.10-3.23 (m, 1H), 3.95 (mc, 1H), 4.19 (mc, 2H), 6.90 (mc, 2H) I-c-24C₂H₅ CH₃ C₂H₅ C₂H₅ CH₃(C═NOCH₃)CH₂CH₂— δ = 1.07 (mc, 6H), 1.26 (mc, 3H),1.80 and 1.83 (in E/Z mixture each case s, Σ 3H), 3.22-3.25 (m, 1H),3.30 and 3.32 syn/anti mixture (in each case s, Σ 3H), 3.98 (mc, 1H),4.20 (mc, 2H), 6.90 (mc, 2H) I-c-25 C₂H₅ CH₃ C₂H₅ C₂H₅C₆H₅CH₂NH(C═O)OCH₂— δ = 1.07 (mc, 6H), 1.25 (mc, 3H), 2.52 (mc, 1H),3.15- syn/anti mixture 3.29 (m, 1H), 4.03 (mc, 1H), 4.11 (mc, 2H), 4.19(mc, 2H), 4.38 (mc, 2H), 6.90 (mc, 2H), 7.08 (mc, 1H), 7.24-7.38 (m, 5H)I-c-26 C₂H₅ CH₃ C₂H₅ C₂H₅ C₆H₅NH(C═O)OCH₂— δ = 1.08 (mc, 6H), 1.25 (t,3H), 2.60 (mc, 1H), 3.18- syn/anti mixture 3.31 (m, 1H), 4.05 (mc, 1H),4.11-4.22 (m, 4H), 6.89 (mc, 2H), 7.08 (mc, 1H), 7.25-7.40 (m, 4H)I-c-27 C₂H₅ CH₃ C₂H₅ C₂H₅ H₂N(C═O)— 72-73° C. syn/anti mixture I-c-28C₂H₅ CH₃ C₂H₅ C₂H₅ H₂N(C═O)OCH₂— δ = 1.09 (mc, 6H), 1.26 (t, 3H), 2.55(mc, 1H), 3.15- syn/anti mixture 3.30 (m, 1H), 4.05 (mc, 1H), 4.07 (d,2H), 4.20 (mc, 2H), 4.60 (s, br, 2H), 6.90 (mc, 2H) I-c-29 C₂H₅ CH₃ C₂H₅C₂H₅ (CH₃)₂N(C═O)— δ = 1.10 (mc, 6H), 1.24 (t, 3H), 2.32 (s, 3H), 2.95(s, syn/anti mixture 3H), 3.06 (s, 3H), 3.25 (mc, 2H), 4.00-4.25 (m,3H), 6.90 (mc, 2H) I-c-30 C₂H₅ CH₃ C₂H₅ C₂H₅ CH₂═CHCH₂—SCH₂— δ = 1.09(mc, 6H), 1.25 (t, 3H), 2.32 (s, 3H), 3.12 (d, syn/anti mixture 2H),3.22 (mc, 1H), 4.00 (mc, 1H), 4.20 (mc, 2H), 4.90 (mc, 2H), 3.72-3.83(m, 1H), 6.90 (mc, 2H)

Example 1 1. Herbicidal Pre-Emergence Action

-   -   Seeds of monocotylidonous and dicotylidonous weed and crop        plants are placed in sandy loam in wood fibre pots and covered        with soil. The test compounds, formulated in the form of        wettable powders (WP), are then, as an aqueous suspension with a        water application rate of 600 l/ha (converted), with 0.2% of        wetting agent added, applied to the surface of the covering soil        in different amounts.    -   After the treatment, the pots are placed in a greenhouse and        kept under good growth conditions for the test plants. The        visual assessment of the emergence damage on the test plants is        carried out after a trial period of three weeks by comparison        with the untreated controls (herbicidal effect in percent: 100%        effect=the plants have died, 0% effect=like control plants).

2. Herbicidal Post-Emergence Action

-   -   Seeds of monocotylidonous and dicotylidonous weed and crop        plants are placed in sandy loam in wood fibre pots, covered with        soil and cultivated in a greenhouse under good growth        conditions. Two to three weeks after sowing, the test plants are        treated at the one-leaf stage. The test compounds, formulated as        wettable powders (WP), are then with a water application rate of        600 l/ha (converted), with 0.2% of wetting agent added, sprayed        onto the green parts of the plants in different amounts. After        the test plants have been kept in the greenhouse under optimum        growth conditions for about three weeks, the effect of the        preparations is assessed visually in comparison to untreated        controls (herbicidal effect in percent: 100% effect=the plants        have died, 0% effect=like control plants).        Post-Emergence, 80 g/ha

Example ALOMY AVEFA ECHCG LOLMU SETVI POLCO VERPE I-a-4 50 90 100 60 100I-a-5 100 100 100 100 100 I-a-7 100 70 100 100 80 I-a-9 100 90 100 100100 I-a-10 100 100 100 100 100 I-a-12 100 100 100 100 100 I-a-13 100 100100 100 100 I-a-22 100 100 100 100 100 I-a-23 70 60 100 90 100 I-a-30 9090 90 I-a-31 90 80 90 90 100 I-a-32 80 90 90 I-a-33 100 100 100 100 90I-a-34 100 100 100 90 I-a-37 100 100 100 100 100 80 I-a-38 90 90 90 90I-a-39 100 100 100 100 I-a-40 100 90 100 90 100 I-a-41 100 100 100 100100 I-a-42 90 100 100 100 100 I-a-60 90 90 100 90 90 I-a-61 90 90 90I-a-79 90 100 100 100 90 100 I-a-81 80 80 80 90 I-b-1 100 100 100 100100 I-b-2 100 100 I-b-3 100 100 100 I-b-23 80 90 100 90 90 I-b-4 100 90100 100 100 I-b-5 100 100 100 100 100 I-c-14 100 100 100 100 100 I-c-1590 90 80 I-c-16 80 80 I-c-17 90 90 90 100 80 I-c-18 100 80 90 100 I-c-21100 100 100 90 I-c-22 80 100 100 100 90 I-c-24 90 80 100 100 100Post-Emergence, 100 g/ha

Example APESV AVEFA PHAMI POAAN SETVI I-c-1 100 80 99 85 97Pre-Emergence, 320 g/ha

Example ALOMY AVEFA ECHCG LOLMU SETVI STEME VERPE VIOTR I-a-4 100 90I-a-5 100 90 100 90 I-a-7 80 100 100 I-a-9 100 80 100 100 90 I-a-10 10090 100 100 100 90 I-a-12 100 80 100 100 I-a-13 80 100 100 90 100 I-a-22100 90 100 100 100 I-a-23 100 90 I-b-1 100 90 100 100 100 90 I-b-2 80 80100 100 90 I-b-3 100 90 100 100 100 90 I-b-4 100 90 100 100 100 90 I-b-5100 100 100 100 90 LOLMU = Lolium multiflorum ALOMY = Alopecurusmyosuroides AVEFA = Avena fatua SETVI = Setaria viridis ECHCG =Echinochloa crus-galli STEME = Stellaria media APESV = Apera spica-ventiPHAMI = Phalaris minor POAAN = Poa annua VERPE = Veronica persica VIOTR= Viola tricolor POLCO = Polygonum convolvulus

Example 2 Tetranychus Test OP-Resistant TETRUR Spray Treatment

Solvents: 78.0 parts by weight of acetone

-   -   1.5 parts by weight of dimethylformamide        Emulsifier: 0.5 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, one part by weightof active compound is mixed with the stated amounts of solvents andemulsifier, and the concentrate is diluted with emulsifier-containingwater to the desired concentration.

Discs of common bean leaves (Phaseolus vulgaris) which are infested byall stages of the common two-spotted spider mite (Tetranychus urticae)are sprayed with an active compound preparation of the desiredconcentration.

After six days, the effect in percent is determined 100% means that allspider mites have been killed; 0% means that none of the spider miteshave been killed.

In this test, for example, the following compounds of the PreparationExamples show an effect of 80% at an application rate of 100 g/ha:

I-c-19, I-c-21

In this test, for example, the following compounds of the PreparationExamples show an effect of 90% at an application rate of 100 g/ha:

I-a-4, I-a-5, I-a-6, I-a-13, I-a-14, I-a-15, I-a-20, I-a-30, I-a-57,I-a-40, I-a-47, I-a-71, I-a-72, I-a-74, I-b-7, I-b-23, I-b-24, I-b-27,I-c-2, I-c-15, I-c-16, I-c-25, I-c-29

In this test, for example, the following compounds of the PreparationExamples show effect of 100% at an application rate of 100 g/ha:

I-a-8, I-a-32, I-b-6, I-b-8, I-b-9, I-b-10, I-c-5, I-c-14, I-c-30

Example 3 Phaedon Test PHAECO Spray Treatment

Solvents: 78.0 parts by weight of acetone

-   -   1.5 parts by weight of dimethylformamide        Emulsifier: 0.5 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, one part by weightof active compound is mixed with the stated amounts of solvents andemulsifier, and the concentrate is diluted with emulsifier-containingwater to the desired concentration.

Discs of Chinese cabbage leaves (Brassica pekinensis) are sprayed withan active compound preparation of the desired concentration and, afterdrying, populated with larvae of the mustard beetle (Phaedoncochleariae).

After 7 days, the effect in % is determined 100% means that all beetlelarvae have been killed; 0% means that none of the beetle larvae havebeen killed.

In this test, for example, the following compounds of the PreparationExamples show an effect of 100% at an application rate of 500 g/ha:I-a-44, I-a-47

Example 4 Myzus Test MYZUPE Spray Treatment

Solvents: 78 parts by weight of acetone

-   -   1.5 parts by weight of dimethylformamide        Emulsifier: 0.5 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, one part by weightof active compound is mixed with the stated amounts of solvents andemulsifier, and the concentrate is diluted with emulsifier-containingwater to the desired concentration.

Discs of Chinese cabbage leaves (Brassica pekinensis) which are infestedby all stages of the green peach aphid (Myzus persicae) are sprayed withan active compound preparation of the desired concentration.

After 6 days, the effect in % is determined 100% means that all aphidshave been killed; 0% means that none of the aphids have been killed.

In this test, for example, the following compounds of the PreparationExamples show an effect of 100% at an application rate of 500 g/ha:I-a-59, I-c-22

The invention claimed is:
 1. A compound of formula (I)

wherein the following isomeric forms can be included:

in which Q represents a bond, a C₁-C₃-alkylene, a C₂-C₃-alkenylene or aC₂-C₃-alkynylene chain, Y represents the groups —OR⁶, —S(O)_(p)R⁶,—CO₂R⁷, —CH═CH₂, cyano, —SCN, —CONR⁸R⁹, —SO₂NR⁸R⁹, —CR¹⁰═O, —NR¹¹R¹²,—CR¹⁰═N—OR¹³, —CR¹⁰═N—R¹⁴, CR¹⁰═N—NR¹⁵R¹⁶, —CR¹⁰(OR¹⁷OR¹⁸),—CR¹⁰(SR¹⁷OR¹⁸), —CR¹⁰(SR¹⁷SR¹⁸), —CR¹⁰(NHR¹⁷NHR¹⁸), —CR¹⁰(NHR¹⁷OR¹⁸),—CR¹⁰(NHR¹⁷SR¹⁸), —CH(CN)₂, —CH(OH)R⁶, halogen, —O(C=M)R¹⁰, —S(C=M)R¹⁰,—O(C=M)NR¹¹R¹², —S(C=M)NR¹¹R¹², —NH(C=M)NR¹¹R¹², —O(C=M)OR⁷, —S(C=M)OR⁷,—NH(C=M)OR⁷ or represents the group W, or Q, Y and R⁵ together form oneof the groups CHCN═, CH(CO₂C₁-C₆-alkyl)═,

W represents a 3- to 7-membered saturated or partially saturatedheterocycle which contains at least one heteroatom optionally oxygen,sulphur or nitrogen and may additionally be mono- or polysubstituted byidentical or different substituents, G represents hydrogen, methyl,ethyl or benzyl (a) or represents one of the groups

E represents a metal ion equivalent, a tertiary sulphonium ion or anammonium ion, L represents oxygen or sulphur, M represents oxygen orsulphur, R¹ represents hydrogen, halogen, cyano, nitro, C₁-C₆-alkyl,halo-C₁-C₆-alkyl, C₃-C₆-cycloalkyl, halo-C₃-C₆-cycloalkyl,C₂-C₆-alkenyl, halo-C₂-C₆-alkenyl, C₂-C₆-alkynyl, halo-C₂-C₆-alkynyl,C₁-C₆-alkoxy, halo-C₁-C₆-alkoxy, C₃-C₆-cycloalkoxy,halo-C₃-C₆-cycloalkoxy, C₂-C₆-alkynyloxy, halo-C₂-C₆-alkynyloxy,C₂-C₆-alkenyloxy, halo-C₂-C₆-alkenyloxy, C₁-C₃-alkylthio,C₁-C₃-alkylsulphinyl, C₁-C₃-alkylsulphonyl, halo-C₁-C₃-alkylthio,halo-C₁-C₃-alkylsulphinyl or halo-C₁-C₃-alkylsulphonyl, R² and R³independently of one another are identical or different and representhydrogen, halogen, cyano, nitro, C₁-C₆-alkyl, halo-C₁-C₆-alkyl,C₂-C₆-alkenyl, halo-C₂-C₆-alkenyl, C₂-C₆-alkynyl, halo-C₂-C₆-alkynyl,C₁-C₆-alkoxy, halo-C₁-C₆-alkoxy, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkoxy,halo-C₃-C₆-cycloalkoxy, C₂-C₆-alkynyloxy, halo-C₂-C₆-alkynyloxy,C₂-C₆-alkenyloxy, halo-C₂-C₆-alkenyloxy, C₁-C₃-alkylthio,C₁-C₃-alkylsulphinyl, C₁-C₃-alkylsulphonyl, halo-C₁-C₃-alkylthio,halo-C₁-C₃-alkylsulphinyl, halo-C₁-C₃-alkylsulphonyl, phenyl or phenylwhich is optionally mono- or polysubstituted by identical or differentsubstituents from the group consisting of halogen, C₁-C₄-alkyl,halo-C₁-C₄-alkyl, C₃-C₆-cycloalkyl, halo-C₃-C₆-cycloalkyl, C₁-C₆-alkoxy,halo-C₁-C₆-alkoxy, nitro and cyano, R⁴ represents hydrogen, halogen,cyano, nitro, C₁-C₆-alkyl, halo-C₁-C₆-alkyl, C₃-C₆-cycloalkyl,halo-C₃-C₆-cycloalkyl, C₁-C₆-alkoxy, halo-C₁-C₆-alkoxy,C₃-C₆-cycloalkoxy, or halo-C₃-C₆-cycloalkoxy, R⁵ represents hydrogen orC₁-C₄-alkyl, R⁶ represents hydrogen, C₁-C₆-alkyl, halo-C₁-C₆-alkyl,C₃-C₆-cycloalkyl, halo-C₃-C₆-cycloalkyl, C₂-C₆-alkenyl,halo-C₂-C₆-alkenyl, C₂-C₆-alkynyl, halo-C₂-C₆-alkynyl,C₁-C₄-alkoxy-C₁-C₄-alkyl, halo-C₁-C₄-alkoxy-C₁-C₄-alkyl,C₃-C₆-cycloalkoxy-C₁-C₄-alkyl, halo-C₃-C₄-cycloalkoxy-C₁-C₄-alkyl,represents benzyl, phenyl, heteroaryl, —CH₂-heteroaryl,—CH₂CH₂-heteroaryl, pyranyl, tetrahydrofuranyl, C₁-C₄-alkanoyl,halo-C₁-C₄-alkanoyl, benzoyl, each of which is optionally mono- orpolysubstituted by identical or different substituents from the groupconsisting of halogen, cyano, nitro, C₁-C₆-alkyl, halo-C₁-C₆-alkyl,C₃-C₆-cycloalkyl, halo-C₃-C₆-cycloalkyl, halo-C₂-C₆-alkenyl,C₂-C₆-alkynyl, halo-C₂-C₆-alkynyl, C₁-C₄-alkoxyalkyl,halo-C₁-C₄-alkoxy-C₁-C₆-alkyl, C₃-C₆-cycloalkoxy-C₁-C₆-alkyl andhalo-C₃-C₆-cycloalkoxy-C₁-C₆-alkyl, or represents benzoyl, which isoptionally mono- or polysubstituted by identical or differentsubstituents from the group consisting of halogen, cyano, nitro,C₁-C₆-alkyl, halo-C₁-C₆-alkyl, C₃-C₆-cycloalkyl andhalo-C₃-C₆-cycloalkyl, R⁷ represents hydrogen, represents in each caseoptionally substituted C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₂-C₆-alkenyl orrepresents a cation E, R⁸ and R⁹ independently of one another areidentical or different and represent hydrogen, C₁-C₆-alkyl,C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, phenyl, benzyl,represent phenyl or benzyl, each of which is mono- or polysubstituted byidentical or different substituents from the group consisting ofhalogen, nitro, cyano and C₁-C₃-alkyl or R⁸ and R⁹ together with theadjacent nitrogen atom form a morpholino, piperidino or pyrrolidinogroup, R¹⁰ represents hydrogen, C₁-C₆-alkyl, halo-C₁-C₄-alkyl,C₂-C₆-alkenyl, halo-C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl,represents phenyl or benzyl, each of which is optionally mono- orpolysubstituted by identical or different substituents from the groupconsisting of halogen, C₁-C₆-alkyl and halo-C₁-C₆-alkyl, R¹¹ and R¹²independently of one another are identical or different and representhydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl,phenyl, benzyl, represent phenyl or benzyl, each of which is mono- orpolysubstituted by identical or different substituents from the groupconsisting of halogen, nitro, cyano and C₁-C₃-alkyl or R¹¹ and R¹²together with the adjacent nitrogen atom form a morpholino, piperidinoor pyrrolidino group, R¹³ represents hydrogen or represents C₁-C₆-alkyl,C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl,C₃-C₆-cycloalkyl-C₁-C₃-alkyl, each of which is optionally interrupted atleast once by oxygen or sulphur and is optionally mono- orpolysubstituted by halogen, represents benzyl or —CH₂-heterocyclyl, eachof which is optionally mono- or polysubstituted by identical ordifferent substituents from the group consisting of halogen, nitro,cyano and C₁-C₃-alkyl, R¹⁴ represents hydrogen, C₁-C₆-alkyl,halo-C₁-C₆-alkyl, C₂-C₆-alkenyl, halo-C₂-C₆-alkenyl, C₂-C₆-alkynyl,halo-C₂-C₆-alkynyl, phenyl, benzyl or represents phenyl or benzyl, eachof which is mono- or polysubstituted by identical or differentsubstituents from the group consisting of halogen, C₁-C₃-alkyl,halo-C₁-C₃-alkyl, C₃-C₆-cycloalkyl, halo-C₃-C₆-cycloalkyl, nitro andcyano, R¹⁵ and R¹⁶ independently of one another are identical ordifferent and represent hydrogen, C₁-C₅-alkyl, C₂-C₆-alkenyl,C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, phenyl, benzyl, represent phenyl orbenzyl, each of which is mono- or polysubstituted by identical ordifferent substituents from the group consisting of halogen, nitro,cyano and C₁-C₃-alkyl or R¹⁵ and R¹⁶ together with the adjacent nitrogenatom form a morpholino, piperidino or pyrrolidino group, R¹⁷ representshydrogen, represents C₁-C₆-alkyl, benzyl or halo-C₁-C₆-alkyl, each ofwhich is optionally interrupted at least once by identical or differentradicals from the group consisting of oxygen and sulphur, R¹⁸ representshydrogen, represents C₁-C₆-alkyl, benzyl or halo-C₁-C₆-alkyl, each ofwhich is optionally interrupted at least once by identical or differentradicals from the group consisting of oxygen and sulphur, R¹⁹ representsoptionally halogen-substituted C₁-C₆-alkyl, C₂-C₆-alkenyl,C₁-C₄-alkoxy-C₁-C₄alkyl, C₁-C₃-alkylthio-C₁-C₄-alkyl,poly-C₁-C₄-alkoxy-C₁-C₄-alkyl or represents C₃-C₆-cycloalkyl which isoptionally mono- or polysubstituted by identical or differentsubstituents from the group consisting of halogen, C₁-C₄-alkyl andC₁-C₄-alkoxy and may optionally be interrupted in the ring by oxygen orsulphur, represents phenyl, phenyl-C₁-C₄-alkyl, hetaryl,phenoxy-C₁-C₄-alkyl or hetaryloxy-C₁-C₄-alkyl, each of which isoptionally substituted by halogen or C₁-C₄-alkyl, R²⁰ representsC₁-C₆-alkyl, C₂-C₆-alkenyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,poly-C₁-C₄-alkoxy-C₁-C₄-alkyl, each of which is optionally mono- orpolysubstituted by identical or different halogen, or representsC₃-C₆-cycloalkyl which may optionally be interrupted in the ring byoxygen or sulphur, or represents benzyl, R²¹, R²² and R²³ independentlyof one another are identical or different and represent C₁-C₆-alkyl,C₁-C₆-alkoxy, C₁-C₆-alkylamino, C₁-C₆-dialkylamino, C₁-C₃-alkylthio,C₂-C₄-alkenylthio, C₃-C₆-cycloalkylthio, each of which is optionallymono- or polysubstituted by identical or different halogen, or representphenyl, benzyl, phenoxy or phenylthio, R²⁴ and R²⁵ independently of oneanother are identical or different and represent hydrogen, representC₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₂-C₆-alkenyl, C₁-C₆-alkoxy,C₁-C₆-alkoxy-C₁-C₄-alkyl, each of which is optionally mono- orpolysubstituted by identical or different halogen, represent phenyl orbenzyl, optionally mono- or polysubstituted by identical or differentsubstituents from the group consisting of halogen and C₁-C₄-alkyl or R²⁴and R²⁵ together with the adjacent nitrogen atom form a morpholino,piperidino or pyrrolidino group, P represents the number 0, 1 or 2, orif Q, Y and R⁵ together represent the group CH₂═, then G representsmethyl, ethyl or benzyl (a).
 2. The compound of formula (I) according toclaim 1, in which Q represents a bond, a C₁-C₃-alkylene, aC₂-C₃-alkenylene or a C₂-C₃-alkynylene chain, Y represents the groups—OR⁶, —S(O)_(p)R⁶, —CO₂R⁷, —CH═CH₂, cyano, —SCN, —CONR⁸R⁹, —SO₂NR⁸R⁹,—CR¹⁰═O, —NR¹¹R¹², —CR¹⁰═N—OR¹³, —CR¹⁰═N—R¹⁴, CR¹⁰═N—NR¹⁵R¹⁶,—CR¹⁰(OR¹⁷OR¹⁸), —CR¹⁰(SR¹⁷OR¹⁸), —CR¹⁰(SR¹⁷SR¹⁸), —CR¹⁰(NHR¹⁷NHR¹⁸),—CR¹⁰(NHR¹⁷OR¹⁸), —CR¹⁰(NHR¹⁷SR¹⁸), —CH(CN)₂, —CH(OH)R⁶, halogen,—O(C=M)R¹⁰, —S(C=M)R¹⁰, —O(C=M)NR¹¹R¹², —S(C=M)NR¹¹R¹², —NH(C=M)NR¹¹R¹²,—O(C=M)OR⁷, —S(C=M)OR⁷, —NH(C=m)OR⁷ or represents the group W, or Q, Yand R⁵ together form one of the groups CHCN═, CH(CO₂C₁-C₆-alkyl)═,

W represents one of the 3- to 7-membered saturated or partiallysaturated heterocycles listed below, which may be attached in variousways and may be mono- or polysubstituted by identical or differentsubstituents from the group consisting of R³¹ and R³²

G represents hydrogen, methyl, ethyl or benzyl (a) or represents one ofthe groups

E represents a metal ion equivalent, a tertiary sulphonium ion or anammonium ion, L represents oxygen or sulphur, M represents oxygen orsulphur, R¹ represents hydrogen, halogen, C₁-C₄-alkyl, halo-C₁-C₄-alkyl,C₃-C₆-cycloalkyl, halo-C₃-C₆-cycloalkyl, C₂-C₄-alkenyl,halo-C₂-C₄-alkenyl, C₂-C₄-alkynyl, halo-C₂-C₄-alkynyl, C₁-C₄-alkoxy,halo-C₁-C₄-alkoxy, C₂-C₄-alkynyloxy, halo-C₂-C₄-alkynyloxy,C₂-C₄-alkenyloxy, halo-C₂-C₄-alkenyloxy, C₁-C₃-alkylthio,C₁-C₃-alkylsulphinyl, C₁-C₃-alkylsulphonyl, halo-C₁-C₃-alkylthio,halo-C₁-C₃-alkylsulphinyl or halo-C₁-C₃-alkylsulphonyl, R² and R³independently of one another are identical or different and representhydrogen, halogen, C₁-C₄-alkyl, halo-C₁-C₄-alkyl, C₂-C₄-alkenyl,halo-C₂-C₄-alkenyl, C₂-C₄-alkynyl, halo-C₂-C₄-alkynyl, C₁-C₄-alkoxy,halo-C₁-C₄-alkoxy, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkoxy,halo-C₃-C₆-cycloalkoxy, C₂-C₄-alkynyloxy, halo-C₂-C₄-alkynyloxy,C₂-C₄-alkenyloxy, halo-C₂-C₄-alkenyloxy, C₁-C₃-alkylthio,C₁-C₃-alkylsulphinyl, C₁-C₃-alkylsulphonyl, halo-C₁-C₃-alkylthio,halo-C₁-C₃-alkylsulphinyl, halo-C₁-C₃-alkylsulphonyl, phenyl or phenylwhich is optionally mono- or polysubstituted by identical or differentsubstituents from the group consisting of halogen, C₁-C₄-alkyl,halo-C₁-C₄-alkyl, R⁴ represents hydrogen, halogen, C₁-C₄-alkyl,halo-C₁-C₄-alkyl, C₃-C₆-cycloalkyl, halo-C₃-C₆-cycloalkyl, C₁-C₄-alkoxy,halo-C₁-C₄-alkoxy, C₃-C₄-cycloalkoxy, or halo-C₃-C₆-cycloalkoxy, R⁵represents hydrogen or C₁-C₄-alkyl, R⁶ represents hydrogen, C₁-C₄-alkyl,halo-C₁-C₄-alkyl, C₃-C₆-cycloalkyl, halo-C₃-C₆-cycloalkyl,C₂-C₄-alkenyl, halo-C₂-C₄-alkenyl, C₂-C₄-alkynyl, halo-C₂-C₄-alkynyl,C₁-C₄-alkoxy-C₁-C₄-alkyl, halo-C₁-C₄-alkoxy-C₁-C₄-alkyl,C₃-C₆-cycloalkoxy-C₁-C₄-alkyl, halo-C₃-C₄-cycloalkoxy-C₁-C₄-alkyl,represents benzyl, phenyl, heteroaryl, —CH₂-heteroaryl,—CH₂CH₂-heteroaryl, C₁-C₄-alkanoyl, halo-C₁-C₄-alkanoyl, benzoyl, eachof which is optionally mono- or polysubstituted by identical ordifferent substituents from the group consisting of halogen, cyano,nitro, C₁-C₄-alkyl, halo-C₁-C₄-alkyl, C₃-C₆-cycloalkyl,halo-C₃-C₆-cycloalkyl, halo-C₂-C₄-alkenyl, C₂-C₄-alkynyl,halo-C₂-C₄-alkynyl, C₁-C₄-alkoxyalkyl, halo-C₁-C₄-alkoxy-C₁-C₆-alkyl,C₃-C₆-cycloalkoxy-C₁-C₆-alkyl and halo-C₃-C₆-cycloalkoxy-C₁-C₆-alkyl, orrepresents benzoyl which is optionally mono- or polysubstituted byidentical or different substituents from the group consisting ofhalogen, cyano, nitro, C₁-C₄-alkyl, halo-C₁-C₄-alkyl, C₃-C₆-cycloalkyland halo-C₃-C₆-cycloalkyl, R⁷ represents hydrogen, representsC₁-C₄-alkyl, C₃-C₆-cycloalkyl, C₂-C₄-alkenyl, each of which isoptionally mono- or polysubstituted by identical or differentsubstituents from the group consisting of halogen and C₁-C₄-alkoxy, orrepresents a cation E, R⁸ and R⁹ independently of one another areidentical or different and represent hydrogen, C₁-C₄-alkyl,C₂-C₄-alkenyl, C₂-C₄-alkynyl, C₃-C₆-cycloalkyl, phenyl, benzyl,represent phenyl or benzyl, each of which is mono- or polysubstituted byidentical or different substituents from the group consisting ofhalogen, nitro, cyano and C₁-C₃-alkyl or R⁸ and R⁹ together with theadjacent nitrogen atom form a morpholino, piperidino or pyrrolidinogroup, R¹⁰ represents hydrogen, C₁-C₄-alkyl, halo-C₁-C₄-alkyl,C₂-C₄-alkenyl, halo-C₂-C₄-alkenyl, C₂-C₄-alkynyl, C₃-C₆-cycloalkyl,represents phenyl or benzyl, each of which is optionally mono- orpolysubstituted by identical or different substituents from the groupconsisting of halogen, C₁-C₄-alkyl and halo-C₁-C₄-alkyl, R¹¹ and R¹²independently of one another are identical or different and representhydrogen, C₁-C₄-alkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl, C₃-C₆-cycloalkyl,phenyl, benzyl, represent phenyl or benzyl, each of which is mono- orpolysubstituted by identical or different substituents from the groupconsisting of halogen and C₁-C₃-alkyl or R¹¹ and R¹² together with theadjacent nitrogen atom form a morpholino, piperidino or pyrrolidinogroup, R¹³ represents hydrogen or represents C₁-C₄-alkyl, C₂-C₄-alkenyl,C₂-C₄-alkynyl, C₃-C₄-cycloalkyl, C₃-C₆-cycloalkyl-C₁-C₃-alkyl, each ofwhich is optionally mono- or polysubstituted by halogen, representsbenzyl or —CH₂-heterocyclyl, each of which is optionally mono- orpolysubstituted by identical or different substituents from the groupconsisting of halogen and C₁-C₃-alkyl, R¹⁴ represents hydrogen,C₁-C₄-alkyl, halo-C₁-C₄-alkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl,halo-C₂-C₄-alkynyl, phenyl, benzyl or represents phenyl or benzyl, eachof which is mono- or polysubstituted by identical or differentsubstituents from the group consisting of halogen, C₁-C₃-alkyl,halo-C₁-C₃-alkyl, C₃-C₆-cycloalkyl, halo-C₃-C₆-cycloalkyl, R¹⁵ and R¹⁶independently of one another are identical or different and representhydrogen, C₁-C₄-alkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl, C₃-C₆-cycloalkyl,phenyl, benzyl, represent phenyl or benzyl, each of which is mono- orpolysubstituted by identical or different substituents from the groupconsisting of halogen and C₁-C₃-alkyl or R¹⁵ and R¹⁶ together with theadjacent nitrogen atom form a morpholino, piperidino or pyrrolidinogroup, R¹⁷ represents hydrogen, represents C₁-C₄-alkyl, benzyl orhalo-C₁-C₄-alkyl, each of which is optionally interrupted at least onceby identical or different radicals from the group consisting of oxygenand sulphur, R¹⁸ represents hydrogen, represents C₁-C₄-alkyl, benzyl orhalo-C₁-C₄-alkyl, each of which is optionally interrupted at least onceby identical or different radicals from the group consisting of oxygenand sulphur, R¹⁹ represents optionally halogen-substituted C₁-C₆-alkyl,C₂-C₆-alkenyl, C₁-C₄-alkoxy-C₁-C₄alkyl, C₁-C₃-alkylthio-C₁-C₄-alkyl,poly-C₁-C₄-alkoxy-C₁-C₄-alkyl or represents C₃-C₆-cycloalkyl which isoptionally mono- or polysubstituted by identical or differentsubstituents from the group consisting of halogen, C₁-C₄-alkyl andC₁-C₄-alkoxy and in which optionally at least one and optionally notmore than two not directly adjacent ring members are replaced by oxygenand/or sulphur, represents in each case optionally halogen- orC₁-C₄-alkyl-substituted phenyl, phenyl-C₁-C₄-alkyl, hetaryl,phenoxy-C₁-C₄-alkyl or hetaryloxy-C₁-C₄-alkyl, R²⁰ representsC₁-C₆-alkyl, C₂-C₆-alkenyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,poly-C₁-C₄-alkoxy-C₁-C₄-alkyl, each of which is optionally mono- orpolysubstituted by identical or different halogen, or representsC₃-C₆-cycloalkyl in which optionally at least one not directly adjacentring members are replaced by oxygen and/or sulphur, or representsbenzyl, R²¹, R²² and R²³ independently of one another are identical ordifferent and represent C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-alkylamino,C₁-C₄-dialkylamino, C₁-C₃-alkylthio, C₂-C₄-alkenylthio,C₃-C₆-cycloalkylthio, each of which is optionally mono- orpolysubstituted by identical or different halogen, or represent phenyl,benzyl, phenoxy or phenylthio, each of which is optionally mono- orpolysubstituted by identical or different substituents from the groupconsisting of halogen, C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₄-haloalkyl,C₁-C₄-haloalkoxy, cyano and nitro, R²⁴ and R²⁵ independently of oneanother are identical or different and represent hydrogen, representC₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₂-C₆-alkenyl, C₁-C₆-alkoxy,C₁-C₆-alkoxy-C₁-C₄-alkyl, each of which is optionally mono- orpolysubstituted by identical or different halogen, represent benzyl orphenyl, optionally mono- or polysubstituted by identical or differentsubstituents from the group consisting of halogen and C₁-C₄-alkyl or R²⁴and R²⁵ together with the adjacent nitrogen atom form a morpholino,piperidino or pyrrolidino group, R³¹ represents halogen, cyano, nitro,C₁-C₆-alkyl, halo-C₁-C₆-alkyl, C₃-C₆-cycloalkyl, halo-C₃-C₆-cycloalkyl,C₂-C₆-alkenyl, halo-C₂-C₆-alkenyl, C₂-C₆-alkynyl, halo-C₂-C₆-alkynyl,C₁-C₆-alkoxy, halo-C₁-C₆-alkoxy, C₃-C₆-cycloalkoxy,halo-C₃-C₆-cycloalkoxy, C₁-C₆-alkynyloxy, halo-C₁-C₆-alkynyloxy,C₂-C₆-alkenyloxy, halo-C₂-C₆-alkenyloxy, C₁-C₃-alkylthio,C₁-C₃-alkylsulphinyl, C₁-C₃-alkylsulphonyl, halo-C₁-C₃-alkylthio,halo-C₁-C₃-alkylsulphinyl, C₁-C₃-alkylsulphonyl, C₁-C₆-alkylcarbonyl,C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylcarbamoyl, amino, C₁-C₆-alkylamino orC₁-C₆-dialkylamino, R³² represents hydrogen, halogen, cyano, nitro,C₁-C₆-alkyl, halo-C₁-C₆-alkyl, C₃-C₆-cycloalkyl, halo-C₃-C₆-cycloalkyl,C₂-C₆-alkenyl, halo-C₂-C₆-alkenyl, C₂-C₆-alkynyl, halo-C₂-C₆-alkynyl,C₁-C₃-alkylsulphonyl, C₁-C₃-alkylsulphonyl, C₁-C₆-alkylcarbonyl,C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylcarbamoyl, amino, C₁-C₆-alkylamino orC₁-C₆-dialkylamino, n represents the number 0, 1, 2, 3, 4, 5 or 6, Prepresents the number 0, 1 or 2, or if Q, Y and R⁵ together representthe group CH₂═, then G represents methyl, ethyl or benzyl (a).
 3. Thecompound according to claim 1, in which if Q represents a bond, —CH₂—,—CH═CH— or —CH₂CH₂—, then Y represents the groups —OR⁶, —CO₂R⁷, —CH═CH₂,cyano, —CR¹⁰═O, —CR¹⁰═N—OR¹³, —CH(OR¹⁷OR¹⁸), S(O)_(p)R⁶, —SCN, —CONR⁸R⁹,—CH(CN)₂, —CH(OH)R⁶, halogen, —OC=MR¹⁰, —S(C=M)R¹⁰, —O(C=M)NR¹¹R¹²,—O(C=M)OR⁷, —NH(C=M)OR⁷, or represents the group W, or Q, Y and R⁵together form one of the groups

W represents

G represents hydrogen, ethyl or benzyl or represents one of the groups

R¹ represents methyl, ethyl, methoxy, ethoxy, halogen or cyclopropyl, R²represents methyl, ethyl or 4-chlorophenyl, R³ represents hydrogen,methyl, ethyl or cyclopropyl, R⁴ represents hydrogen, methyl or ethyl,R⁵ represents hydrogen, R⁶ represents hydrogen, methyl, ethyl,—CH₂—CH(CH₃)₂, —CH₂—CH═CH₂, cyano, trifluoromethyl, methoxymethyl,2-benzoxazolyl, 4,5-dimethylthiazol-2-yl, 2-oxazolyl, 2-tetrahydrofurylor the 2-pyranyl group, R⁷ represents hydrogen, methyl, ethyl, isopropylor n-propyl, R⁸ represents hydrogen or methyl, R⁹ represents hydrogen ormethyl, or R⁸ and R⁹ together with the nitrogen atom form the group

R¹⁰ represents hydrogen, methyl, t-butyl, fluoromethyl, difluoromethylor trifluoromethyl, R¹¹ represents hydrogen or methyl, R¹² representshydrogen, methyl, benzyl or phenyl, R¹³ represents hydrogen, methyl,isopropyl, —CH₂CH═CCl₂, —CH₂CH═CH₂, —CH₂C≡CH or —CH₂C₃H₅, R¹⁷ representsmethyl, ethyl or n-propyl R¹⁸ represents methyl, ethyl or n-propyl, R¹⁹represents C₁-C₄-alkyl R²⁰ represents methyl, ethyl or isopropyl, prepresents 0 or 2, M represents oxygen or sulphur, or if Q, Y and R⁵together represent the group CH₂═, then G represents methyl, ethyl orbenzyl (a).
 4. The compound according to claim 1, in which Q representsa bond, —CH₂—, —CH₂CH₂— or —CH═CH—, Y represents the groups —OR⁶,—CO₂R⁷, —CH═CH₂, cyano, —CR¹⁰═O, —CR¹⁰═N—OR¹³, —CH(OR¹⁷OR¹⁸),S(O)_(p)R⁶, —SCN, —CONR⁸R⁹, —CH(CN)₂, —CH(OH)R⁶, bromine, —O(C═O)R¹⁰,—S(C═P)R¹⁰, —O(C═O)NR¹¹R¹², or represents the group W, or Q, Y and R⁵together form one of the groups

W represents

G represents hydrogen, ethyl, benzyl (a) or represents one of the groups

R¹ represents methyl or ethyl, R² represents methyl, R³ representshydrogen, R⁴ represents methyl or ethyl, R⁵ represents hydrogen, R⁶represents hydrogen, methyl, ethyl, —CH₂—CH(CH₃)₂, —CH₂—CH═CH₂,trifluoromethyl, methoxymethyl, 2-benzoxazolyl,4,5-dimethylthiazol-2-yl, 2-oxazolyl, 2-tetrahydrofuryl or the 2-pyranylgroup, R⁷ represents hydrogen, methyl or ethyl, R⁸ represents hydrogenor methyl, R⁹ represents hydrogen or methyl, or R⁸ and R⁹ together withthe nitrogen atom represent the group

R¹⁰ represents hydrogen, methyl, t-butyl or trifluoromethyl, R¹¹represents hydrogen or methyl, R¹² represents hydrogen, methyl, benzylor phenyl, R¹³ represents hydrogen, methyl, isopropyl, —CH₂CH═CCl₂,—CH₂CH═CH₂, —CH₂C≡CH or —CH₂C₃H₅, R¹⁷ represents methyl or ethyl, R¹⁸represents methyl or ethyl, R¹⁹ represents ethyl, tert-butyl orisopropyl, R²⁰ represents methyl, ethyl or isopropyl, P represents 0 or2.
 5. The compound according to claim 1, in which Q, Y and R⁵ togetherrepresent the group CH₂=, G represents benzyl (a), R¹ represents ethyl,R² represents methyl, R³ represents hydrogen, R⁴ represents ethyl.
 6. Acomposition for controlling pests and/or unwanted vegetation, comprisingat least one compound of the formula (I) according to claim
 1. 7. Amethod for controlling animal pests and/or unwanted vegetation,comprising applying said compound of the formula (I) according to claim1, to pests, unwanted vegetation and/or a habitat thereof.
 8. Thecompound of the formula (I) according to claim 1, capable of being usedfor controlling animal pests and/or unwanted vegetation.
 9. A processfor preparing a composition for controlling pests and/or unwantedvegetation, comprising mixing said compound of the formula (I) accordingto claim 1 with an extender and/or surfactant.
 10. A compositioncomprising an effective amount of an active compound combinationcomprising, as components, (a′) at least one compound of the formula (I)according to claim 1 and (b′) at least one crop plantcompatibility-improving compound.
 11. A method for controlling unwantedvegetation, comprising applying said composition according to claim 10to a plant and/or surroundings thereof.
 12. The composition according toclaim 10, capable of being used for controlling unwanted vegetation. 13.A method for controlling unwanted vegetation, comprising applying saidcompound of the formula (I) according to claim 1, and a crop plantcompatibility-improving compound to a plant and/or surroundings thereofseparately in close temporal succession.
 14. A method for controllingunwanted vegetation, comprising applying a compound of the formula (I)according to claim 10 and the crop plant compatibility-improvingcompound to a plant and/or surroundings thereof separately in closetemporal succession.